2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 218792-61-1
• Molecular Formula: C₄₉H₆₃NO₁₃Si
• Molecular Weight: 902.124

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl 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: 60.0%

allyl 6-O-trimethylacetyl-β-D-galactopyranosyl bromide + (3S,6S,8S,8aS)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester (218792-61-1)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; at -78 ℃; for 2h;

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

Reference yield: 75.0%

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester (218792-61-1) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-((3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yloxy)-tetrahydro-pyran-2-ylmethyl ester (218792-71-3)

Guidance literature:

With pyridine; hydrogen fluoride; for 4h; Ambient temperature;

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

Reference yield:

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(3S,6S,8S,8aS)-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester (218792-61-1) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-6-[(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]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (218792-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / HF, pyridine / 4 h / Ambient temperature

2: 71 percent / CuBr₂, Bu₄nBr / CH₂Cl₂ / 16 h / Ambient temperature

3: 80 percent / NaOMe / 5 h / 0 °C

With pyridine; hydrogen fluoride; tetrabutylammomium bromide; sodium methylate; copper(ll) bromide; In dichloromethane;

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

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-((3S,6S,8S,8aS)-8-benzyloxy-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yloxy)-tetrahydro-pyran-2-ylmethyl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-6-[(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]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

C₅₇H₇₁NO₁₆

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(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]-tetrahydro-pyran-2-ylmethyl ester

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