(1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

Base Information

Chemical Name:(1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate
CAS No.:1476028-78-0
Molecular Formula:C₂₇H₃₅N₃O₇Si
Molecular Weight:541.676
Hs Code.:

Synonyms:(1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

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Chemical Property of (1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

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Technology Process of (1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

There total 10 articles about (1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate 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: 91.0%

: 1476028-76-8
(3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate

: 1476028-78-0
(1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

Guidance literature:: With ruthenium trichloride; sodium periodate; water; In acetonitrile; at 20 ℃; for 4h;
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

: 1476028-78-0
(1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium azide / ethanol / 3 h / Reflux

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

3: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C

4: dmap; triethylamine / ethyl acetate / 1 h / 0 °C

5: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C

With dmap; ruthenium trichloride; sodium periodate; sodium azide; water; diisobutylaluminium hydride; triethylamine; In ethanol; hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/ejoc.201300804

Reference yield:

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

: 1476028-78-0
(1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate

Guidance literature:: Multi-step reaction with 4 steps

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

2: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C

3: dmap; triethylamine / ethyl acetate / 1 h / 0 °C

4: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C

With dmap; ruthenium trichloride; sodium periodate; water; diisobutylaluminium hydride; triethylamine; In hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/ejoc.201300804