(3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

Base Information

Chemical Name:(3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate
CAS No.:1476028-74-6
Molecular Formula:C₂₅H₃₁N₃O₄Si
Molecular Weight:465.624
Hs Code.:

Synonyms:(3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

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Chemical Property of (3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

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Technology Process of (3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

There total 6 articles about (3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate 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: 90.0%

: 1476028-72-4
(3S,4R,5R)-5-azido-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1476028-74-6
(3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1002/ejoc.201300804

Reference yield:

: 1476028-70-2
(3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

: 1476028-74-6
(3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium azide / ethanol / 3 h / Reflux

2: dmap; triethylamine / dichloromethane / 5 h / 20 °C

With dmap; sodium azide; triethylamine; In ethanol; dichloromethane;
DOI:10.1002/ejoc.201300804

Reference yield:

: 101769-63-5
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

: 1476028-74-6
(3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: thionyl chloride / 0.5 h / 20 °C

1.2: 0 - 20 °C

2.1: potassium carbonate / ethanol / 20 h / 20 °C

3.1: triethylamine / dichloromethane / 1 h / 0 °C

4.1: trifluoroacetic acid; water / 8 h / 20 °C

5.1: sodium azide / ethanol / 3 h / Reflux

6.1: dmap; triethylamine / dichloromethane / 5 h / 20 °C

With dmap; thionyl chloride; sodium azide; water; potassium carbonate; triethylamine; trifluoroacetic acid; In ethanol; dichloromethane;
DOI:10.1002/ejoc.201300804