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

Base Information

• Chemical Name: (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol
• CAS No.: 474526-55-1
• Molecular Formula: C₂₁H₃₂N₂O₇SSi
• Molecular Weight: 484.646
• Mol file: 474526-55-1.mol

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

Chemical Property of (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol

There total 3 articles about (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-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:

tert-butyldimethylsilyl chloride (18162-48-6) + N-((3aS,4R,7S,7aR)-7-Hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl)-4-nitro-benzenesulfonamide → (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol (474526-55-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 25 ℃; for 9h;

DOI:10.1021/jo020155k

Reference yield:

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (80409-75-2,343865-40-7) → (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol (474526-55-1)

Guidance literature:

Multi-step reaction with 3 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

With chiral chloronitroso synthon; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo020155k

Reference yield:

(1S,4R,5S,6R)-(-)-4-Amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol (137775-67-8) → (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol (474526-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / acetonitrile / 8 h / 25 °C

2: 3.78 g / DBU / acetonitrile / 9 h / 25 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In acetonitrile;

DOI:10.1021/jo020155k

upstream raw materials:

tert-butyldimethylsilyl chloride

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole

(1S,4R,5S,6R)-(-)-4-Amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol

Downstream raw materials:

N-[2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-hexahydro-1,3,5-trioxa-cyclopropa[f]inden-6-yl]-N-(4-methoxy-benzo[1,3]dioxol-5-ylmethyl)-4-nitro-benzenesulfonamide

(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

narciclasine

(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-nitrobenzenesulfonyl)-1,1a,2,3,4,4a,6-heptahydrophenanthridine