Tri-O-benzyl-D-glucal

Base Information

• Chemical Name: Tri-O-benzyl-D-glucal
• CAS No.: 55628-54-1
• Molecular Formula: C27H28 O4
• Molecular Weight: 416.517
• Hs Code.: 29329900
• DSSTox Substance ID: DTXSID70471566
• Nikkaji Number: J273.880E,J646.052F
• Wikidata: Q72509843
• Mol file: 55628-54-1.mol

Synonyms:3,4,6-tri-O-benzyl-D-glucal;3,4,6-tri-O-benzylglucal

Chemical Property of Tri-O-benzyl-D-glucal

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 2.24E-11mmHg at 25°C
• Melting Point: 57-58 °C(lit.)
• Refractive Index: -2 ° (C=2.5, CH3CN)
• Boiling Point: 544.9 °C at 760 mmHg
• Flash Point: 129.7 °C
• PSA: 36.92000
• Density: 1.16 g/cm³
• LogP: 5.28650
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Water Solubility.: Insoluble in water, easily soluble in CHCl3
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 416.19875937
• Heavy Atom Count: 31
• Complexity: 503

Purity/Quality:

99% ^*data from raw suppliers

3,4,6-Tri-O-benzyl-D-galactal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 24/25-45-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C=CO2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H](C=CO2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Uses: 3,4,6-Tri-O-benzyl-D-glucal, is an important building block for both solid- and solution-phase synthesis of oligosaccharides.

Technology Process of Tri-O-benzyl-D-glucal

There total 182 articles about Tri-O-benzyl-D-glucal 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: 100.0%

benzyl bromide (100-39-0) + D-glucal (13265-84-4) → 3,4,6-tri-O-benzyl-D-glucal (55628-54-1)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(02)00872-9

Reference yield: 100.0%

phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-allo-pyranoside → (2R,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran (55628-54-1,80040-79-5,71049-35-9)

Guidance literature:

With sodium acetate; copper; acetic acid; zinc; In tetrahydrofuran; at 0 - 20 ℃; for 6h;

DOI:10.1021/ol052866l

Reference yield: 100.0%

phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside (653575-98-5) → 3,4,6-tri-O-benzyl-D-glucal (55628-54-1)

Guidance literature:

With sodium acetate; copper; acetic acid; zinc; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1021/ol052866l

upstream raw materials:

1,2-didehydrodideoxyallose

benzyl bromide

1,5-anhydro-3,6-di-O-acetyl-2-deoxy-D-ribo-hex-1-enitol

3,4,6-tri-O-acetyl-D-glucal

Downstream raw materials:

1,2-anhydro-3,4,6-tri-O-benzyl-β-D-altropyranose

C₂₇H₂₉FO₅

C₂₇H₂₉FO₅

C₂₇H₂₉FO₅

Refernces

• 1、 Guo, Zhen-Yan,Liu, Kai-Meng,Liu, Meng,Liu, Miao,Qin, Xian-Jin,Wang, Peng-Yu,Xiong, De-Cai,Xue, Wan-Ying,Ye, Xin-Shan. "Iterative Synthesis of 2-Deoxyoligosaccharides Enabled by Stereoselective Visible-Light-Promoted Glycosylation". . . Retrieved 2022/02/21.
• 2、 Li, Gefei,Noguchi, Masato,Arisaka, Genki,Tanaka, Yuuki,Shoda, Shin-Ichiro. "A protecting group-free approach for synthesizingC-glycosides through glycosyl dithiocarbamates". supporting information. p. 3134 - 3138. Retrieved 2021/04/21.