tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

Base Information

Chemical Name:tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate
CAS No.:1429183-74-3
Molecular Formula:C₂₇H₃₉NO₆Si
Molecular Weight:501.695
Hs Code.:

Synonyms:tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

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Chemical Property of tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

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Technology Process of tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

There total 8 articles about tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate 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: 97.0%

: 1429183-73-2
tert-butyl (1S,2R,6R)-2-(tert-butyldiphenylsilyloxy)-6-hydroxycyclohex-3-enylcarbamate

: 1429183-74-3
tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 24h; stereoselective reaction;
DOI:10.1055/s-0032-1317962

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1429183-74-3
tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1: 1H-imidazole / dichloromethane / 4 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

4: tetrahydrofuran; diethyl ether / -78 - -30 °C

5: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux; Inert atmosphere

6: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 24 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; osmium(VIII) oxide; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1055/s-0032-1317962

Reference yield:

: 114301-34-7,114301-35-8,117487-58-8,122709-37-9,117487-60-2
(2S,3S)-2-amino-N-<(tert-butyloxy)carbonyl>-1,3-dihydroxy-1,2-O,N-isopropylidene-4-pentene

: 1429183-74-3
tert-butyl (1S,2S,3S,4S,6R)-2-(tert-Butyldiphenylsilyloxy)-3,4,6-trihydroxycyclohexylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1: 1H-imidazole / dichloromethane / 4 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

4: tetrahydrofuran; diethyl ether / -78 - -30 °C

5: Grubbs catalyst first generation / dichloromethane / 16 h / Reflux; Inert atmosphere

6: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 24 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; osmium(VIII) oxide; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1055/s-0032-1317962