Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

Base Information

• Chemical Name: Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester
• CAS No.: 218792-55-3
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384

Synonyms:Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

Chemical Property of Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

Chemical Property:

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Technology Process of Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

There total 2 articles about Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-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: 78.0%

Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yl ester (218792-68-8) → Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester (218792-55-3)

Guidance literature:

With pyridine; hydrogen fluoride; at 0 ℃; for 4h;

DOI:10.1016/S0960-894X(98)00500-9

Reference yield:

(3S,6S,8S,8aS)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one → Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester (218792-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 1 h / Ambient temperature

2: 78 percent / HF, pyridine / 4 h / 0 °C

With pyridine; hydrogen fluoride;

DOI:10.1016/S0960-894X(98)00500-9

Reference yield: 70.0%

2,3,4-tri-O-benzyl-β-L-fucopyranosyl 2-thiopyridyl carbonate (160776-15-8) + Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester (218792-55-3) → Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-5-oxo-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yl ester

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1016/S0960-894X(98)00500-9

upstream raw materials:

Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yl ester

Downstream raw materials:

[(3S,6S,8S,8aS)-8-Hydroxy-5-oxo-3-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl ester

(3S,6S,8S,8aS)-8-Benzyloxy-6-hydroxy-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-hexahydro-indolizin-5-one

[(3S,6S,8S,8aS)-8-Benzyloxy-5-oxo-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-octahydro-indolizin-6-yloxy]-phenyl-acetic acid methyl ester

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