(1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

Base Information

Chemical Name:(1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine
CAS No.:444988-70-9
Molecular Formula:C₂₃H₃₇NO₅Si
Molecular Weight:435.636
Hs Code.:

Synonyms:(1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

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Chemical Property of (1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

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Technology Process of (1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

There total 6 articles about (1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine 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%

: 444988-68-5
(1S,2R,8aS)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,2,3,5,8,8a-hexahydro-indolizine-6-carboxylic acid methyl ester

: 444988-70-9
(1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)00005-4

Reference yield:

: 220875-15-0
(5S,6S,7R)-1,2-diaza-6-benzyloxy-7-hydroxy-3-oxo-[3.3.0]bicyclooctane

: 444988-70-9
(1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

Guidance literature:: Multi-step reaction with 6 steps

1: aq. Raney nickel / 1.5 h / 20 °C / pH 7

2: HCl / 4 h

3: 0.23 g / imidazole / acetonitrile / 20 °C

4: 96 percent / Et₃N / ethanol / 20 h / 20 °C

5: 65 percent / HN(i-Pr)2; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -30 °C

6: 78 percent / NaBH₄ / methanol / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; nickel; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; acetonitrile; 5: Dieckmann cyclization;
DOI:10.1016/S0040-4020(02)00005-4

Reference yield:

: 220875-27-4
2-((2S,3S,4R)-3-Benzyloxy-4-hydroxy-pyrrolidin-2-yl)-acetamide

: 444988-70-9
(1S,2R,6S,7S,8aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-7-hydroxy-6-methoxycarbonyl-indolizidine

Guidance literature:: Multi-step reaction with 5 steps

1: HCl / 4 h

2: 0.23 g / imidazole / acetonitrile / 20 °C

3: 96 percent / Et₃N / ethanol / 20 h / 20 °C

4: 65 percent / HN(i-Pr)2; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -30 °C

5: 78 percent / NaBH₄ / methanol / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; acetonitrile; 4: Dieckmann cyclization;
DOI:10.1016/S0040-4020(02)00005-4