Methyl 2,3-di-O-benzylhexopyranoside

Base Information

• Chemical Name: Methyl 2,3-di-O-benzylhexopyranoside
• CAS No.: 17791-36-5
• Molecular Formula: C21H26 O6
• Molecular Weight: 374.434
• Hs Code.: 2938909090
• NSC Number: 170185,92309
• DSSTox Substance ID: DTXSID10293789
• Nikkaji Number: J3.167.505G
• Mol file: 17791-36-5.mol

Synonyms:Methyl 2,3-di-O-benzylhexopyranoside;17791-36-5;2-(hydroxymethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol;methyl 2,3-di-O-benzyl-alpha-D-glucopyranoside;NSC92309;SCHEMBL21706804;DTXSID10293789;AOHYQGVMTDLXSL-UHFFFAOYSA-N;NSC-92309;NSC170185;NSC-170185;SB48865;Methyl 2,3-di-O-benzylhexopyranoside #;Methyl .alpha.-d-glucoside, 2,3-dibenzyl-

Chemical Property of Methyl 2,3-di-O-benzylhexopyranoside

Chemical Property:

• Vapor Pressure: 2.3E-12mmHg at 25°C
• Melting Point: 76-81°C
• Boiling Point: 537.1°Cat760mmHg
• Flash Point: 278.6°C
• PSA: 77.38000
• Density: 1.24g/cm³
• LogP: 1.88170
• Storage Temp.: ?20°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 374.17293854
• Heavy Atom Count: 27
• Complexity: 408

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2,3-di-O-benzyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3

Technology Process of Methyl 2,3-di-O-benzylhexopyranoside

There total 110 articles about Methyl 2,3-di-O-benzylhexopyranoside 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%

methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,13225-19-9,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9) → methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5)

Guidance literature:

With methanol; iodine; for 4h; Heating;

DOI:10.1021/jo051792o

Reference yield: 98.0%

methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (90633-88-8) → methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5)

Guidance literature:

With sodium hydrogensulfate monohydrate; In methanol; at 21 - 28 ℃; for 1h;

DOI:10.1055/s-0033-1338469

Reference yield: 97.0%

methyl 2,3-di-O-benzyl-4,6-(2,6-dimethylbenzylidene)-α-D-mannopyranoside (1610712-48-5) → methyl 2,3-di-O-benzyl-α-D-mannopyranoside (6988-40-5,17791-36-5,29388-46-3,31873-34-4,33164-03-3,52526-60-0,61117-12-2,87392-25-4,117605-35-3,51842-19-4)

Guidance literature:

With iodine; In methanol; water; for 3.5h; Reflux;

DOI:10.1016/j.carres.2014.02.024

upstream raw materials:

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

acetic acid

methyl 2,3-di-O-benzyl-4,6-di-O-isopropylidene-β-D-glucopyranoside

benzyl bromide

Downstream raw materials:

Tetradecanoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxycarbonyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside

methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate

methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranoside

Refernces

• 1、 Johansson, Rolf,Samuelsson, Bertil. "Regioselective Reductive Ring Opening of 4-Methoxybenzylidene Acetals of Hexopyranosides. Access to a Novel Protective Group Strategy". . p. 201 - 202. Retrieved 1984.
• 2、 Bagi, Péter,Bakó, Péter,Heged?s, László,Orbán, István,Rapi, Zsolt,Varga, Bertalan. "Synthesis of methyl 4,6-di-o-ethyl-α-d-glucopyranoside-based azacrown ethers and their effects in asymmetric reactions". . . Retrieved 2021/08/12.
• 3、 Mez?, Erika,Herczeg, Mihály,Demeter, Fruzsina,Bereczki, Ilona,Csávás, Magdolna,Borbás, Anikó. "Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6- O-Halobenzylidene Acetals of Glucopyranosides". . p. 12973 - 12987. Retrieved 2021/09/18.