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

Base Information

Chemical Name:(2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol
CAS No.:130859-97-1
Molecular Formula:C₂₀H₂₉NO₇
Molecular Weight:395.453
Hs Code.:

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

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

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

There total 6 articles about (2S,3S,4S,5R)-5-<(benzyloxycarbonyl)amino>-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol 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%

: 130281-95-7
(2S,3S,4S,5R)-5-amino-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol

: 501-53-1,94274-21-2
benzyl chloroformate

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

Guidance literature:: With sodium carbonate; In dichloromethane; water; for 3h; Ambient temperature;
DOI:10.1021/jo00002a057

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With hydrogen; sodium carbonate; 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

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

Guidance literature:: Multi-step reaction with 6 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

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