6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Base Information

• Chemical Name: 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester
• CAS No.: 178271-52-8
• Molecular Formula: C₄₉H₆₁NO₁₂
• Molecular Weight: 856.023

Synonyms:6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Chemical Property of 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

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Technology Process of 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

There total 3 articles about 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl 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:

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite (153659-02-0) → 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (178271-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / 4A molecular sieves, ZnCl₂, AgClO₄ / CH₂Cl₂ / 1 h / -15 °C

2: 1.) borane-triethylamine complex, 4A molecular sieves, 2.) AlCl₃ / 1.) THF, RT, 30 min, 2.) THF, RT, 18 h

With aluminium trichloride; triethylamine-borane; 4 A molecular sieve; silver perchlorate; zinc(II) chloride; In dichloromethane;

DOI:10.1021/ja952265x

Reference yield:

6-((2R,4aR,6R,7R,8R,8aS)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-hexanoic acid methyl ester → 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (178271-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / 4A molecular sieves, ZnCl₂, AgClO₄ / CH₂Cl₂ / 1 h / -15 °C

2: 1.) borane-triethylamine complex, 4A molecular sieves, 2.) AlCl₃ / 1.) THF, RT, 30 min, 2.) THF, RT, 18 h

With aluminium trichloride; triethylamine-borane; 4 A molecular sieve; silver perchlorate; zinc(II) chloride; In dichloromethane;

DOI:10.1021/ja952265x

Reference yield:

6-[(2R,4aR,6R,7R,8R,8aS)-7-Acetylamino-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-hexanoic acid methyl ester (178271-56-2) → 6-[(2R,3R,4R,5S,6R)-3-Acetylamino-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester (178271-52-8)

Guidance literature:

With aluminium trichloride; triethylamine-borane; 4 A molecular sieve; Yield given. Multistep reaction; 1.) THF, RT, 30 min, 2.) THF, RT, 18 h;

DOI:10.1021/ja952265x

upstream raw materials:

6-[(2R,4aR,6R,7R,8R,8aS)-7-Acetylamino-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-hexanoic acid methyl ester

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite

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