(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester
CAS No.:198289-42-8
Molecular Formula:C₂₈H₃₈O₇Si
Molecular Weight:514.691
Hs Code.:

(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

Synonyms:(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

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Chemical Property of (1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

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Technology Process of (1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

There total 12 articles about (1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid 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: 81.0%

: 198289-41-7
(2R,4aR,5S,8aS)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-2-phenyl-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid methyl ester

: 198289-42-8
(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: With water; In acetic acid; at 80 ℃; for 1h;
DOI:10.1021/jo970960c

Reference yield:

: 107550-83-4
(2E,4E)-hexa-2,4-diene-1,6-diol

: 198289-42-8
(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 95 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 35 percent / BHT / 42 h / 150 °C

3: 88 percent / HF*Et₃N / acetonitrile / 42 h / 40 °C

4: 91 percent / K₂CO₃ / 1 h / Ambient temperature

5: 64 percent / ZnCl₂ / diethyl ether / 1 h / Ambient temperature

6: 95 percent / pyridine / 20 h / Ambient temperature

7: 173 mg / MCPBA, NaHCO₃ / CHCl₃ / 18 h / Ambient temperature

8: 112 mg / K₂CO₃ / methanol / 1.5 h / 0 °C

9: 65 percent / (COCl)2 / dimethylsulfoxide; triethylamine / 1 h / -78 - 20 °C

10: 91 percent / DIPEA / CH₂Cl₂ / 16 h / Ambient temperature

11: 91 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

12: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

13: 81 percent / H₂O / acetic acid / 1 h / 80 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; water; sodium hydrogencarbonate; potassium carbonate; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In pyridine; methanol; diethyl ether; dichloromethane; chloroform; acetic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo970960c

Reference yield:

: 106726-68-5
(6E,8E)-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradeca-6,8-diene

: 198289-42-8
(1S,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-6-hydroxymethyl-5-methoxymethoxy-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 35 percent / BHT / 42 h / 150 °C

2: 88 percent / HF*Et₃N / acetonitrile / 42 h / 40 °C

3: 91 percent / K₂CO₃ / 1 h / Ambient temperature

4: 64 percent / ZnCl₂ / diethyl ether / 1 h / Ambient temperature

5: 95 percent / pyridine / 20 h / Ambient temperature

6: 173 mg / MCPBA, NaHCO₃ / CHCl₃ / 18 h / Ambient temperature

7: 112 mg / K₂CO₃ / methanol / 1.5 h / 0 °C

8: 65 percent / (COCl)2 / dimethylsulfoxide; triethylamine / 1 h / -78 - 20 °C

9: 91 percent / DIPEA / CH₂Cl₂ / 16 h / Ambient temperature

10: 91 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

11: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

12: 81 percent / H₂O / acetic acid / 1 h / 80 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; water; sodium hydrogencarbonate; potassium carbonate; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In pyridine; methanol; diethyl ether; dichloromethane; chloroform; acetic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo970960c