(1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

Base Information

Chemical Name:(1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol
CAS No.:69240-16-0
Molecular Formula:C₂₆H₃₈O₈S₂Si
Molecular Weight:570.8
Hs Code.:

Synonyms:(1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

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Chemical Property of (1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

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Technology Process of (1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

There total 12 articles about (1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol 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: 85.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 57357-88-7,61476-30-0
(1R,2S,3R,5R)-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

: 69240-16-0
(1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1016/S0008-6215(00)85704-3

Reference yield:

: 53397-94-7
(-)-(1S,2R,4R,6R)-1,2-Cyclohexylidenedioxycyclohexane-4,6-diol

: 69240-16-0
(1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

Guidance literature:: Multi-step reaction with 6 steps

2: acid hydrolysis

3: sodium methoxide / methanol

4: 70 percent / pyridine / 0 °C

5: 90 percent / sulfuric acid (0.75M) / 1,2-dimethoxy-ethane / 2.5 h / Heating

6: 85 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; sulfuric acid; sodium methylate; In pyridine; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)85704-3

Reference yield:

: 53397-93-6
3-O,4-O-cyclohexylidene-(3R,4S,5R)-trihydroxycyclohexan-1-one

: 69240-16-0
(1R,2S,3R,5R)-3-O-tert-butyldimethylsilyl-1,5-di-O-tosylcyclohexane-1,2,3,5-tetrol

Guidance literature:: Multi-step reaction with 7 steps

1: 57 percent / lithium borohydride / bis-(2-methoxy-ethyl) ether / 4 h / 0 °C

3: acid hydrolysis

4: sodium methoxide / methanol

5: 70 percent / pyridine / 0 °C

6: 90 percent / sulfuric acid (0.75M) / 1,2-dimethoxy-ethane / 2.5 h / Heating

7: 85 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; lithium borohydride; sulfuric acid; sodium methylate; In pyridine; methanol; 1,2-dimethoxyethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)85704-3