(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Base Information

• Chemical Name: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol
• CAS No.: 162118-38-9
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.532
• Mol file: 162118-38-9.mol

Synonyms:(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Chemical Property of (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

There total 26 articles about (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-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: 90.0%

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside (183875-25-4) → (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9)

Guidance literature:

With N-iodosaccharine; In water; acetonitrile; at 20 ℃; for 0.05h;

DOI:10.1055/s-2007-977412

Reference yield: 82.3%

p-chlorophenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside → (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9)

Guidance literature:

With N-iodo-succinimide; water; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1039/b914193f

Reference yield: 82.0%

1-O-acetyl-2,3,4-tri-O-benzyl-β-L-fucopyranose (146815-26-1) → (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9)

Guidance literature:

With perchloric acid; In acetonitrile; at 70 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.03.050

upstream raw materials:

perbenzyl fucosyl bromide

phenyl 2-acetamido-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside

6-(trifluoroacetamido)hexyl 2-acetamido-2-deoxy-4,6-O-(p-methoxybenzylidene)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

2-methoxyethyl 2,3,4-tri-O-benzyl-β-L-fucopyranoside

Downstream raw materials:

2-((3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-pyridine

perbenzyl fucosyl bromide

2,3,4-tri-O-benzyl-β-L-fucopyranosyl 2-thiopyridyl carbonate

1-O-acetyl-2,3,4-tri-O-benzyl-α-L-fucopyranose