[(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

Base Information

Chemical Name:[(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
CAS No.:218792-64-4
Molecular Formula:C₅₂H₅₇NO₁₀
Molecular Weight:856.025
Hs Code.:

[(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

Synonyms:[(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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Chemical Property of [(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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Technology Process of [(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

There total 5 articles about [(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 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: 93.0%

: 22979-35-7
Methyl phenyldiazoacetate

: 218792-58-6
(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

: 218792-64-4
[(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

Guidance literature:: With dirhodium tetraacetate; for 12h; Ambient temperature;
DOI:10.1016/S0960-894X(98)00500-9

Reference yield:

: 218792-55-3
Acetic acid (3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

: 218792-64-4
[(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

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / CuBr₂, Bu₄NBr / CH₂Cl₂ / 16 h / Ambient temperature

2: 91 percent / NaOMe / 1 h / Ambient temperature

3: 93 percent / Rh₂(OAc)4 / 12 h / Ambient temperature

With dirhodium tetraacetate; tetrabutylammomium bromide; sodium methylate; copper(ll) bromide; In dichloromethane;
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

: 218792-64-4
[(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

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 70 percent / CuBr₂, Bu₄NBr / CH₂Cl₂ / 16 h / Ambient temperature

4: 91 percent / NaOMe / 1 h / Ambient temperature

5: 93 percent / Rh₂(OAc)4 / 12 h / Ambient temperature

With pyridine; dirhodium tetraacetate; hydrogen fluoride; tetrabutylammomium bromide; sodium methylate; copper(ll) bromide; In dichloromethane;
DOI:10.1016/S0960-894X(98)00500-9