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

Base Information

• Chemical Name: (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexene-1,2-diol
• CAS No.: 475275-62-8
• Molecular Formula: C₂₂H₃₅NO₅SSi
• Molecular Weight: 453.675
• Mol file: 475275-62-8.mol

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

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

There total 1 articles about (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)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: 78.0%

(1S,4R,5S,6R)-(-)-4-Amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol (137775-67-8) + tert-butyldimethylsilyl chloride (18162-48-6) + p-toluenesulfonyl chloride (98-59-9) → (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexene-1,2-diol (475275-62-8)

Guidance literature:

(1S,4R,5S,6R)-(-)-4-Amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol; p-toluenesulfonyl chloride; With triethylamine; In acetonitrile; at 25 ℃; for 8h;

tert-butyldimethylsilyl chloride; In acetonitrile; at 25 ℃; for 9h;

DOI:10.1016/S0040-4020(02)00736-6

Reference yield: 91.0%

3,4-Methylenedioxybenzyl bromide (2606-51-1) + (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexene-1,2-diol (475275-62-8) → (1R,2R,3S,4S,5S,6R)-4,5-(isopropylidenedioxy)-3-[(tert-butyldimethylsilyl)oxy]-6-N-(3',4'-methylenedioxybenzyl)-N-(4'-methylphenylsulfonyl)-7-oxabicyclo[4.1.0]heptane (393165-27-0)

Guidance literature:

(1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexene-1,2-diol; With N-Bromosuccinimide; In water; acetone; at 25 ℃; for 10h;

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at 20 ℃; for 8h;

3,4-Methylenedioxybenzyl bromide; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1016/S0040-4020(02)00736-6

Reference yield:

(1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexene-1,2-diol (475275-62-8) → (1S,2S,3S,4S,5S,6R)-5-bromo-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexane-1,2,4-triol + (1S,2S,3R,4S,5R,6R)-4-bromo-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-toluenesulfonyl)amino)cyclohexane-1,2,5-triol

Guidance literature:

With N-Bromosuccinimide; In water; acetone; at 25 ℃; for 10h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(02)00736-6

upstream raw materials:

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

tert-butyldimethylsilyl chloride

p-toluenesulfonyl chloride

Downstream raw materials:

(1R,2R,3S,4S,5S,6R)-4,5-(isopropylidenedioxy)-3-[(tert-butyldimethylsilyl)oxy]-6-N-(3',4'-methylenedioxybenzyl)-N-(4'-methylphenylsulfonyl)-7-oxabicyclo[4.1.0]heptane

(1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-5-(p-toluenesulfonyl)-1,2,3,4,4a,5,6,10b-octahydrophenanthridine