(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

Base Information

Chemical Name:(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane
CAS No.:130859-98-2
Molecular Formula:C₂₁H₃₁NO₉S
Molecular Weight:473.544
Hs Code.:

Synonyms:(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

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Chemical Property of (2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

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Technology Process of (2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

There total 7 articles about (2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane 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: 96.0%

: 130859-97-1
(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol

: 124-63-0
methanesulfonyl chloride

: 130859-98-2
(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

Guidance literature:: With triethylamine; In dichloromethane; 1.) 0 degC, 1 h 2.) rt, 1 h;
DOI:10.1021/jo00002a057

Reference yield:

: 130114-46-4
(2S,3S,4S,5R)-5-azido-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol

: 130859-98-2
(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / H₂ / 10percent Pd-C / methanol / 4 h

2: 97 percent / aq. Na₂CO₃ / CH₂Cl₂; H₂O / 3 h / Ambient temperature

3: 96 percent / triethylamine / CH₂Cl₂ / 1.) 0 degC, 1 h 2.) rt, 1 h

With hydrogen; sodium carbonate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; water;
DOI:10.1021/jo00002a057

Reference yield:

: 130193-61-2
(2R,3S,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol

: 130859-98-2
(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)-1-<(methylsulfonyl)oxy>hexane

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / Li₂NiBr₄ / tetrahydrofuran / 6 h / Heating

2: 66 percent / pyridinium p-toluenesulfonate / acetone / 1.) rt, 20 h 2.) reflux, 2 h

3: 98 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / Ambient temperature

4: 65 percent / sodium azide / dimethylsulfoxide / 4 h / 120 °C

5: 81 percent / H₂ / 10percent Pd-C / methanol / 4 h

6: 97 percent / aq. Na₂CO₃ / CH₂Cl₂; H₂O / 3 h / Ambient temperature

7: 96 percent / triethylamine / CH₂Cl₂ / 1.) 0 degC, 1 h 2.) rt, 1 h

With sodium azide; dilithium tetrabromonickelate(II); tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jo00002a057