Methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside

Base Information

• Chemical Name: Methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside
• CAS No.: 139978-92-0
• Molecular Formula: C₁₄H₂₆O₁₁
• Molecular Weight: 370.354
• DSSTox Substance ID: DTXSID50930681
• Wikidata: Q82906097
• Mol file: 139978-92-0.mol

Synonyms:MDMHG;methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside

Chemical Property of Methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside

Chemical Property:

• Vapor Pressure: 1.25E-19mmHg at 25°C
• Boiling Point: 649.7°Cat760mmHg
• Flash Point: 346.7°C
• PSA: 178.53000
• Density: 1.57g/cm³
• LogP: -4.35300
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 370.14751164
• Heavy Atom Count: 25
• Complexity: 410

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CCO)O)O)O)O)O
• Isomeric SMILES: CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)CCO)O)O)O)O)O

Technology Process of Methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside

There total 3 articles about Methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside 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:

methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside (51842-16-1) → methyl 4-O-(6-deoxy-α-D-manno-heptopyranosyl)-β-galactopyranoside (139978-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / N-iodosuccinimide, molecular sieves 4 Angstroem / triflic acid / 1,2-dichloro-ethane; diethyl ether / 0.08 h / Ambient temperature

2: 1) sodium methoxide, 2) hydrogen / 2) Pd/C (10percent) / 1) methanol, 18h, room temperature, 2) 2-propanol, water, acetic acid, 24h, room temperature

With N-iodo-succinimide; 4 A molecular sieve; hydrogen; sodium methylate; palladium on activated charcoal; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(92)84105-2

Reference yield:

ethyl 2,3,4,7-tetra-O-benzoyl-6-deoxy-1-thio-α,β-D-manno-heptopyranoside (139978-89-5,139978-95-3) → methyl 4-O-(6-deoxy-α-D-manno-heptopyranosyl)-β-galactopyranoside (139978-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / N-iodosuccinimide, molecular sieves 4 Angstroem / triflic acid / 1,2-dichloro-ethane; diethyl ether / 0.08 h / Ambient temperature

2: 1) sodium methoxide, 2) hydrogen / 2) Pd/C (10percent) / 1) methanol, 18h, room temperature, 2) 2-propanol, water, acetic acid, 24h, room temperature

With N-iodo-succinimide; 4 A molecular sieve; hydrogen; sodium methylate; palladium on activated charcoal; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(92)84105-2

Reference yield:

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,7-O-benzoyl-6-deoxy-α-D-manno-heptopyranosyl)-β-D-galactopyranoside (139978-91-9) → methyl 4-O-(6-deoxy-α-D-manno-heptopyranosyl)-β-galactopyranoside (139978-92-0)

Guidance literature:

With hydrogen; sodium methylate; palladium on activated charcoal; Yield given. Multistep reaction; 1) methanol, 18h, room temperature, 2) 2-propanol, water, acetic acid, 24h, room temperature;

DOI:10.1016/0008-6215(92)84105-2

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,7-O-benzoyl-6-deoxy-α-D-manno-heptopyranosyl)-β-D-galactopyranoside

methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside

ethyl 2,3,4,7-tetra-O-benzoyl-6-deoxy-1-thio-α,β-D-manno-heptopyranoside