(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Base Information

Chemical Name:(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one
CAS No.:639820-24-9
Molecular Formula:C₂₉H₃₁NO₅Si
Molecular Weight:501.654
Hs Code.:

Synonyms:(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

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Chemical Property of (1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

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Technology Process of (1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

There total 7 articles about (1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 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%

: 501-53-1,94274-21-2
benzyl chloroformate

: 639820-23-8
(1R,4S,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-6-(3',4'-dimethoxybenzyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

: 639820-24-9
(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Guidance literature:: (1R,4S,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-6-(3',4'-dimethoxybenzyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 24h;

benzyl chloroformate; With pyridine; dmap; In dichloromethane; water; at 20 ℃; for 2h;
DOI:10.1002/ejoc.200801000

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: (1R,4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexan-2-one

: 639820-24-9
(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Guidance literature:: With pyridine; dmap; In dichloromethane; water; at 20 ℃; for 2h;
DOI:10.1021/jo035039b

Reference yield:

: 92512-33-9
(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

: 639820-24-9
(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / pyridine / CH₂Cl₂ / 3.25 h / -78 - -25 °C

2: 64 percent / dimethylformamide / 0.5 h / -60 °C

3: DDQ / CH₂Cl₂; H₂O / 24 h / 20 °C

4: 1.29 g / pyridine; DMAP / CH₂Cl₂; H₂O / 2 h / 20 °C

With pyridine; dmap; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo035039b