1,3:4,6-Di-O-benzylidene-D-mannitol

Base Information

• Chemical Name: 1,3:4,6-Di-O-benzylidene-D-mannitol
• CAS No.: 28224-73-9
• Molecular Formula: C20H22O6
• Molecular Weight: 358.391
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID401292783
• Nikkaji Number: J1.594.700D
• Mol file: 28224-73-9.mol

Synonyms:1,3:4,6-Di-O-benzylidene-D-mannitol;28224-73-9;(4R,4'R,5R,5'R)-2,2'-Diphenyl-[4,4'-bi(1,3-dioxane)]-5,5'-diol;(4R,5R)-4-[(4R,5R)-5-HYDROXY-2-PHENYL-1,3-DIOXAN-4-YL]-2-PHENYL-1,3-DIOXAN-5-OL;SCHEMBL1038804;NVEGGHPETXMRSV-NIJYPJQDSA-N;DTXSID401292783;AKOS027320438;1,3:4,6-Di-O-benzyliden-D-mannitol;CS-W009793;1,3:4,6-di-O-ben-zylidene-d-mannitol;BS-42545;1-O,3-O:4-O,6-O-Dibenzylidene-D-mannitol;1,3:4,6-bis-O-(phenylmethylene)-D-Mannitol;E84509;W-202181;1,3:4,6-Di-O-benzylidene-D-mannitol, >=98.0% (sum of enantiomers, HPLC)

Chemical Property of 1,3:4,6-Di-O-benzylidene-D-mannitol

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Vapor Pressure: 5.05E-15mmHg at 25°C
• Melting Point: 192-195°C
• Refractive Index: 1.6
• Boiling Point: 595.4 °C at 760 mmHg
• PKA: 12.96±0.60(Predicted)
• Flash Point: 313.9 °C
• PSA: 77.38000
• Density: 1.312 g/cm³
• LogP: 1.93660
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), Methanol ()Slightly
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 358.14163842
• Heavy Atom Count: 26
• Complexity: 394

Purity/Quality:

99% ^*data from raw suppliers

1,3:4,6-Di-O-benzylidene-D-mannitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC(O1)C2=CC=CC=C2)C3C(COC(O3)C4=CC=CC=C4)O)O
• Isomeric SMILES: C1[C@H]([C@@H](OC(O1)C2=CC=CC=C2)[C@H]3[C@@H](COC(O3)C4=CC=CC=C4)O)O
• Uses: 1,3:4,6-Di-O-benzylidene-D-mannitol (cas# 28224-73-9) is a compound useful in organic synthesis.

Technology Process of 1,3:4,6-Di-O-benzylidene-D-mannitol

There total 6 articles about 1,3:4,6-Di-O-benzylidene-D-mannitol 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: 45.0%

mannitol (69-65-8) + benzaldehyde (100-52-7) → 1,3:4,6-di-O-benzylidene-D-mannitol (28224-73-9)

Guidance literature:

With sulfuric acid; In N,N-dimethyl-formamide; for 76h;

DOI:10.1016/S0040-4039(98)01361-6

Reference yield: 20.0%

mannitol (69-65-8) + benzaldehyde dimethyl acetal (1125-88-8) → 1,3:4,6-di-O-benzylidene-D-mannitol (28224-73-9)

Guidance literature:

With sulfuric acid; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 120h; Inert atmosphere;

DOI:10.1039/c3ob40899j

Reference yield:

D-galactitol (608-66-2) + benzaldehyde (100-52-7) → D-O1,O3;O4,O6-((R,S)-dibenzylidene)-galactitol (5349-07-5,28224-73-9,61490-28-6,80041-29-8)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01253a036

upstream raw materials:

D-galactitol

benzaldehyde

mannitol

benzaldehyde dimethyl acetal

Downstream raw materials:

1,3:4,6-di-O-benzylidene-2,5-di-O-benzyl-D-Mannitol

1,3:4,6-di-O-benzylidene-2,5-di-O-allyl-D-mannitol

N-amino-1,3:4,6-di-O-benzylidene-2,5-dideoxy-2,5-imino-L-iditol

1,3:4,6-di-O-benzylidene-2,5-O-methylene-D-mannitol

Refernces

• 1、 Zhao, Yingwei,Huang, Hanmin,Shao, Jianping,Xia, Chungu. "Readily available and recoverable chiral ionic phosphite ligands for the highly enantioselective hydrogenation of functionalized olefins". scheme or table. p. 769 - 774. Retrieved 2011/08/06.
• 2、 Esposito, Annamaria,Falorni, Massimo,Taddei, Maurizio. "Synthesis of amphiphilic polyhydroxylated pyrrolidines as potential glycosidase inhibitors". . p. 6543 - 6546. Retrieved 2007/10/03.