methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 1256155-25-5
• Molecular Formula: C₄₇H₅₄O₁₄
• Molecular Weight: 842.937
• Mol file: 1256155-25-5.mol

Synonyms:methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

There total 5 articles about methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside 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: 91.0%

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide (29741-69-3) → methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside (1256155-25-5)

Guidance literature:

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol; 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide; With silver(l) oxide; 3,3-difluoro-1,3-dihydro-2H-indol-2-one; In dichloromethane; at 20 ℃; for 0.5h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1021/acs.joc.7b02768

Reference yield:

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + 3,4,6-tri-O-acetyl-2-O-benzyl-D-glucopyranosyl nitrate → methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside + methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside (1256155-25-5)

Guidance literature:

With ytterbium(III) triflate; In diethyl ether; 1,2-dichloro-ethane; at 20 ℃; for 18h; Overall yield = 40 %; diastereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/ejoc.201801272

Reference yield:

3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide → methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside + methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside (1256155-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: silver nitrate / acetonitrile / 0.08 h / 20 °C

2: ytterbium(III) triflate / diethyl ether; 1,2-dichloro-ethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

With silver nitrate; ytterbium(III) triflate; In diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/ejoc.201801272

upstream raw materials:

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

2-thiazolinyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-glucopyranoside

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide

ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside