(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

Base Information

Chemical Name:(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol
CAS No.:474526-57-3
Molecular Formula:C₃₄H₄₇N₃O₁₂SSi
Molecular Weight:749.912
Hs Code.:

(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

Synonyms:(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

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Chemical Property of (1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

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Technology Process of (1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

There total 8 articles about (1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol 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%

: 450408-41-0
diethyl-carbamic acid 5-bromomethyl-benzo[1,3]dioxol-4-yl ester

: 474526-55-1
(1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol

: 474526-57-3
(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

Guidance literature:: (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol; With N-Bromosuccinimide; In water; acetone; at 20 ℃; for 10h;

diethyl-carbamic acid 5-bromomethyl-benzo[1,3]dioxol-4-yl ester; With potassium carbonate; In acetonitrile; at 60 ℃; for 4h; Further stages.;
DOI:10.1021/jo020155k

Reference yield:

: 80409-75-2,343865-40-7
cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole

: 474526-57-3
(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: chiral chloronitroso synthon / CH₂Cl₂ / 12 h / 0 °C

1.2: 85 percent / Al-Hg / acetonitrile; H₂O / 1.5 h / 20 °C

2.1: Et₃N / acetonitrile / 8 h / 25 °C

3.1: 3.78 g / DBU / acetonitrile / 9 h / 25 °C

4.1: NBS / H₂O; acetone / 10 h / 20 °C

4.2: 88 percent / K₂CO₃ / acetonitrile / 4 h / 60 °C

With N-Bromosuccinimide; chiral chloronitroso synthon; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/jo020155k

Reference yield:

: 23780-59-8
4-hydroxybenzo[d][1,3]dioxole-5-carbaldehyde

: 474526-57-3
(1S,2S,3S,4R,5R,6S)-3-((t-butyldimethylsilyl)oxy)-6-(N-(o-carbamoyloxypiperonyl)-N-(p-nitrobenzenesulfonyl)amino)-4,5-epoxy-1,2-O-isopropylidenecyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: K₂CO₃ / acetonitrile / 2 h / 85 °C

2.1: NaBH₄ / methanol / 0 - 25 °C

3.1: HBr / CH₂Cl₂; H₂O / 25 °C

4.1: NBS / H₂O; acetone / 10 h / 20 °C

4.2: 88 percent / K₂CO₃ / acetonitrile / 4 h / 60 °C

With sodium tetrahydroborate; N-Bromosuccinimide; hydrogen bromide; potassium carbonate; In methanol; dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/jo020155k