Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 149717-37-3
• Molecular Formula: C₂₆H₃₁O₁₀P
• Molecular Weight: 534.5
• Mol file: 149717-37-3.mol

Synonyms:Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 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:

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) → Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (149717-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: BnNH₂ / tetrahydrofuran / Ambient temperature

2: 1,2,4-triazole / CH₂Cl₂ / 2 h / Ambient temperature

With 1,2,4-Triazole; benzylamine; In tetrahydrofuran; dichloromethane;

Reference yield:

dibenzyl N,N-diethylphosphoramidite (67746-43-4) + 2,3,4-tri-O-acetyl-L-fucopyranose (28915-80-2,40591-53-5,40591-54-6,40591-55-7,120449-19-6,120449-20-9,143332-42-7,148081-39-4,151413-57-9,151413-58-0) → Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (149717-37-3)

Guidance literature:

With 1,2,4-Triazole; In dichloromethane; for 2h; Ambient temperature;

Reference yield: 67.0%

Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (149717-37-3) + para-thiocresol (106-45-6) → (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (153658-86-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/jo00083a032

upstream raw materials:

dibenzyl N,N-diethylphosphoramidite

2,3,4-tri-O-acetyl-L-fucopyranose

1,2,3,4-tetra-O-acetyl-L-fucopyranose

Downstream raw materials:

dibenzylphosphoryl 2,3,4-tri-O-acetyl-L-fucoside

dibenzyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl phosphate

dibenzyl 2,3,4-tri-O-acetyl-β-L-fucopyranosyl phosphate

(2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate