(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

Base Information

Chemical Name:(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate
CAS No.:1287225-43-7
Molecular Formula:C₄₀H₄₇NO₉S
Molecular Weight:717.88
Hs Code.:

Synonyms:(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

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Chemical Property of (1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

Chemical Property:

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Technology Process of (1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

There total 1 articles about (1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate 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: 88.0%

: 1287225-40-4
(1S,2S,3R,4R,5S,6S)-N-(2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexyl)carbamic acid tert-butyl ester

: 124-63-0
methanesulfonyl chloride

: 1287225-43-7
(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

Guidance literature:: With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 5h;
DOI:10.1021/ja111480z

Reference yield: 63.0%

: 1287225-43-7
(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

: 1287225-44-8
(3aR,4S,5R,6S,7S,7aR)-4,5,6,7-tetrakis(benzyloxy)-hexahydrobenzo[d]oxazol-2(3H)-one

Guidance literature:: In N,N-dimethyl-formamide; at 110 ℃; for 16h;
DOI:10.1021/ja111480z

Reference yield:

: 1287225-43-7
(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate

: 1287226-85-0
(3aR,4S,5S,6S,7R,7aR)-4-(benzyloxy)-3-nonyl-2-(nonylimino)-octahydrobenzo[d]oxazole-5,6,7-triol

Guidance literature:: Multi-step reaction with 6 steps

1.1: N,N-dimethyl-formamide / 16 h / 110 °C

2.1: ethanol; sodium hydroxide / 16 h / 80 °C

3.1: sodium cyanoborohydride; acetic acid / methanol / 4 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 18 h / 45 °C

5.1: mercury(II) oxide / toluene / 115 °C / Inert atmosphere

6.1: boron trichloride / n-heptane; dichloromethane / 7 h / -78 - -40 °C

6.2: -78 °C

With ethanol; boron trichloride; sodium cyanoborohydride; acetic acid; mercury(II) oxide; sodium hydroxide; In tetrahydrofuran; methanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja111480z