Diacetone L-sorbose

Base Information

• Chemical Name: Diacetone L-sorbose
• CAS No.: 17682-70-1
• Deprecated CAS: 15383-42-3,3768-12-5,70587-93-8
• Molecular Formula: C12H20 O6
• Molecular Weight: 260.287
• Hs Code.: 29400090
• European Community (EC) Number: 605-783-8
• DSSTox Substance ID: DTXSID60891870
• Nikkaji Number: J1.805.922C
• Wikidata: Q72462481
• Mol file: 17682-70-1.mol

Synonyms:17682-70-1;Diacetone L-sorbose;2,3:4,6-Di-O-isopropylidene-alpha-L-sorbofuranose;alpha-L-Sorbofuranose, 2,3:4,6-bis-o-(1-methylethylidene)-;2,3:4,6-Di-O-isopropylidene-L-sorbofuranose;((3aS,3bR,7aS,8aS)-2,2,5,5-Tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxin-8a-yl)methanol;[(1R,2S,6R,8S)-4,4,11,11-Tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-6-yl]methanol;[(1R,2S,6S,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-6-yl]methanol;Diaceton-L-sorbose;2,3,4,6-Di-O-Isopropylidene-alpha-L-sorbofuranose;SCHEMBL3307263;DTXSID60891870;GQXSDDHYUVYJCQ-NHRVJRKFSA-N;AKOS015896913;2,3:4,6-Di-O-isopropylidene-?-L-sorbofuranose;2-O,3-O:4-O,6-O-Diisopropylidene-alpha-L-sorbofuranose;2,3:4,6-Di-O-isopropylidene-alpha-L-sorbofuranose, >=98% (TLC);2,3,4,6-Di-O-isopropylidene-|A inverted exclamation mark-L-sorbofuranose

Chemical Property of Diacetone L-sorbose

Chemical Property:

• Appearance/Colour: White, microcrystalline solid
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Melting Point: 80-81ºC
• Boiling Point: 329.3 °C at 760 mmHg
• PKA: 14.66±0.10(Predicted)
• Flash Point: 153 °C
• PSA: 66.38000
• Density: 1.181 g/cm³
• LogP: 0.37680
• Storage Temp.: ?20°C
• Solubility.: Acetone, Dichloromethane
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 260.12598835
• Heavy Atom Count: 18
• Complexity: 355

Purity/Quality:

98% or more ^*data from raw suppliers

2,3:4,6-Di-O-isopropylidene-a-L-sorbofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC2C(O1)C3C(O2)(OC(O3)(C)C)CO)C
• Isomeric SMILES: CC1(OC[C@H]2[C@@H](O1)[C@H]3[C@@](O2)(OC(O3)(C)C)CO)C
• Uses: 2,3:4,6-Di-O-isopropylidene-α-L-sorbofuranose (cas# 17682-70-1) is a compound useful in organic synthesis.

Technology Process of Diacetone L-sorbose

There total 14 articles about Diacetone L-sorbose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

L-sorbofuranose (36468-68-5) + acetone (67-64-1) → 2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1)

Guidance literature:

With diphenylphosphinopolystyrene; iodine; at 20 ℃; for 0.5h;

DOI:10.1055/s-2005-918521

Reference yield: 89.0%

L-sorbose (87-79-6,18875-34-8) + acetone (67-64-1) → 2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1)

Guidance literature:

With iodine; at 20 ℃; for 15h;

DOI:10.1016/j.tetlet.2021.153072

Reference yield: 89.0%

dikegulac (18467-77-1) → 2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1016/S0957-4166(00)80392-4

upstream raw materials:

L-sorbose

1-O-(Phenylacetyl)-2,3:4,6-di-O-isopropyliden-β-L-sorbofuranose

acetone

L-sorbopyranose

Downstream raw materials:

1-O-p-methoxybenzyl-2,3-O-isopropylidene-α-L-sorbofuranose

1-O-p-methoxybenzyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose

1-O-acetyl-2,3-O-isopropylidene-α-L-sorbofuranose

Refernces

• 1、 Nadtochii,Burova,Vasil'eva,Melent'eva. "Synthesis of diacetone-L-sorbose". . p. 229 - 230. Retrieved 2001.
• 2、 Van Grunenberg et al.. "-". . p. 1507. Retrieved 1938.
• 3、 Gurjar,Das,Sadalapure. "Zaragozic acid: Unusual stereochemical dependence in anhydride formation of carbohydrate templates". . p. 1933 - 1936. Retrieved 1995.
• 4、 Rodygin, Konstantin S.,Werner, Irina,Ananikov, Valentine P.. "A Green and Sustainable Route to Carbohydrate Vinyl Ethers for Accessing Bioinspired Materials with a Unique Microspherical Morphology". . p. 292 - 298. Retrieved 2018.
• 5、 Yu, Shuai,Liu, Yinxin,Shang, Chengxiang,Du, Yuguo,Liu, Jun. "A carbohydrate-based approach for the total synthesis of sawaranospirolide C". supporting information. . Retrieved 2021/04/22.
• 6、 Gurjar, Mukund K.,Yellol, Gorakh S.,Mohapatra, Debendra K.. "A carbohydrate-based synthesis of the C13-C22 fragment of amphidinolide X". scheme or table. p. 1753 - 1758. Retrieved 2012/06/01.