Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

Base Information

Chemical Name:Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester
CAS No.:130009-53-9
Molecular Formula:C₂₃H₃₈O₄S₂Si
Molecular Weight:470.77
Hs Code.:

Synonyms:Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

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Chemical Property of Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

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Technology Process of Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

There total 11 articles about Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester 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: 80.0%

: 75-15-0,12122-00-8
carbon disulfide

: 130009-52-8
(1R,2R,3R,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexanol

: 74-88-4
methyl iodide

: 130009-53-9
Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

Guidance literature:: With sodium hydride; at 70 ℃; for 3.5h;
DOI:10.1016/S0040-4039(00)89010-3

Reference yield:

: 129952-17-6
(E)-(2R,3R)-2-Methoxy-8-trimethylsilanyl-oct-6-ene-1,3-diol

: 130009-53-9
Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

2: 73 percent / NaH / dimethylformamide / 18 h / 0 to 20 deg C

3: 84 percent / pyridinium p-toluenesulfonate / methanol / 3.5 h / 50 °C

4: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / 1 h / -60 °C

5: BF₃-Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

6: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) H₂O, MeOH, 0 to 40 deg C, 3 h

7: 78 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

8: 80 percent / NaH / 3.5 h / 70 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)89010-3

Reference yield:

: 129952-16-5
(E)-(2S,3R)-3-Hydroxy-2-methoxy-8-trimethylsilanyl-oct-6-enoic acid methyl ester

: 130009-53-9
Dithiocarbonic acid O-[(1R,2S,3R,6R)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 84 percent / LiAlH₄ / diethyl ether / 3 h / 0 to 20 deg C

2: 96 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

3: 73 percent / NaH / dimethylformamide / 18 h / 0 to 20 deg C

4: 84 percent / pyridinium p-toluenesulfonate / methanol / 3.5 h / 50 °C

5: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / 1 h / -60 °C

6: BF₃-Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) H₂O, MeOH, 0 to 40 deg C, 3 h

8: 78 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

9: 80 percent / NaH / 3.5 h / 70 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)89010-3