methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside
• CAS No.: 116391-15-2
• Molecular Formula: C₄₈H₅₄O₁₀
• Molecular Weight: 790.951
• Mol file: 116391-15-2.mol

Synonyms:methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside

Chemical Property of methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside

There total 9 articles about methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-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:

(2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol (53685-11-3) + p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (211801-54-6,807361-40-6) → C48H54O10 + methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside (116391-15-2)

Guidance literature:

p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside; With trifluoromethylsulfonic anhydride; di(p-tolyl) sulfoxide; In dichloromethane; at -60 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

(2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol; In dichloromethane; at -60 - -40 ℃; for 4h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetlet.2017.04.056

Reference yield:

1,2,3,4-tetra-O-acetyl-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4) → C48H54O10 + methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside (116391-15-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere; Molecular sieve

2.1: sodium methylate / methanol / 3.5 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

3.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

4.1: di(p-tolyl) sulfoxide; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -60 °C / Inert atmosphere; Molecular sieve

4.2: 4 h / -60 - -40 °C / Inert atmosphere; Molecular sieve

With trifluoromethylsulfonic anhydride; di(p-tolyl) sulfoxide; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetlet.2017.04.056

Reference yield:

(2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (153658-86-7) → C48H54O10 + methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside (116391-15-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 3.5 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

2.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

3.1: di(p-tolyl) sulfoxide; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -60 °C / Inert atmosphere; Molecular sieve

3.2: 4 h / -60 - -40 °C / Inert atmosphere; Molecular sieve

With trifluoromethylsulfonic anhydride; di(p-tolyl) sulfoxide; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetlet.2017.04.056

upstream raw materials:

(2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

methyl 3,4-O-isopropylidene-α-D-galactopyranoside

methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside