(2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol
• CAS No.: 112107-25-2
• Molecular Formula: C₆₁H₇₀O₁₃
• Molecular Weight: 1011.22
• Mol file: 112107-25-2.mol

Synonyms:

Chemical Property of (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol

There total 4 articles about (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol 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 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol (112107-25-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) benzene, reflux, 14 h, 2.) benzene, 65 deg C, 2 h

2: 1.) 4 Angstroem molecular sieves, 3.) sodium methoxide / 2.) trimethylsilyl trifluoromethanesulfonate / 1.) dichloromethane, room temperature, 30 min, 2.) dichloromethane, 2 h, 3.) methanol, 4 h

With 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; di(n-butyl)tin oxide; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1139/v87-459

Reference yield:

benzyl bromide (100-39-0) → (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol (112107-25-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) benzene, reflux, 14 h, 2.) benzene, 65 deg C, 2 h

2: 1.) 4 Angstroem molecular sieves, 3.) sodium methoxide / 2.) trimethylsilyl trifluoromethanesulfonate / 1.) dichloromethane, room temperature, 30 min, 2.) dichloromethane, 2 h, 3.) methanol, 4 h

With 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; di(n-butyl)tin oxide; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1139/v87-459

Reference yield:

methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside (69558-07-2) → (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol (112107-25-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 76.5 percent / concentrated sulfuric acid / 0.5 h

2: 1.) 4 Angstroem molecular sieves, 3.) sodium methoxide / 2.) trimethylsilyl trifluoromethanesulfonate / 1.) dichloromethane, room temperature, 30 min, 2.) dichloromethane, 2 h, 3.) methanol, 4 h

With 4 A molecular sieve; sulfuric acid; sodium methylate; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1139/v87-459

upstream raw materials:

methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside

1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranose

methyl 4-O-benzyl-α-L-rhamnopyranoside

benzyl bromide