(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

Base Information

Chemical Name:(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid
CAS No.:1380312-71-9
Molecular Formula:C₃₀H₅₁NO₈Si₂
Molecular Weight:609.908
Hs Code.:

Synonyms:(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

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Chemical Property of (1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

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Technology Process of (1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

There total 6 articles about (1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid 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:

: C₁₈H₂₃NO₈

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1380312-71-9
(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

Guidance literature:: With 1H-imidazole; In methanol; N,N-dimethyl-formamide; at 80 ℃; for 17h; Inert atmosphere;
DOI:10.1002/ejoc.201200103

Reference yield:

: 1380312-70-8
methyl (1R,2R,3S,4R,5S,6R)-2-(benzyloxycarbonylamino)-5,6-dihydroxy-3,4-(isopropylidenedioxy)cyclohexanecarboxylate

: 1380312-71-9
(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: barium hydroxide octahydrate / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere

2: 1H-imidazole / methanol; N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere

With 1H-imidazole; barium hydroxide octahydrate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200103

Reference yield:

: 1380312-69-5
methyl (1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2-hydroxy-4,5-(isopropylidenedioxy)-6-nitrocyclohexanecarboxylate

: 1380312-71-9
(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen; citric acid / methanol / 48 h / 20 °C / 760.05 Torr

2: sodium hydrogencarbonate / methanol; water / 3 h / 0 - 20 °C / Inert atmosphere

3: barium hydroxide octahydrate / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere

4: 1H-imidazole / methanol; N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere

With 1H-imidazole; barium hydroxide octahydrate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; citric acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200103