(3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester
CAS No.:111649-67-3
Molecular Formula:C₃₅H₄₆O₆Si
Molecular Weight:590.832
Hs Code.:

(3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

Synonyms:(3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

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Chemical Property of (3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

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Technology Process of (3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

There total 29 articles about (3aR,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic 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: 32.0%

: 111649-66-2,118490-67-8,118490-68-9,118490-69-0,120053-55-6
(E)-(R)-5-{(4S,5R)-5-[(1Z,3Z)-7-(tert-Butyl-diphenyl-silanyloxy)-hepta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-oxo-hex-2-enoic acid methyl ester

: 111649-67-3,118490-70-3,118490-71-4,118490-72-5,118490-75-8,118490-76-9,118490-77-0
(3aS,4R,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

: 118490-77-0
(3aS,4R,5aR,6R,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

: 118490-75-8
(3aS,4R,5aS,6S,7S,9aR,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

Guidance literature:: With iodine; In hexane; at 23 ℃; for 48h;
DOI:10.1021/jo00265a036

Reference yield:

: 88424-95-7
2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol

: 111649-67-3,118490-70-3,118490-71-4,118490-72-5,118490-75-8,118490-76-9,118490-77-0
(3aS,4R,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: AcOH / H₂O

2: Et₃N, DMAP / CH₂Cl₂

3: p-TsOH

4: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) 2 h

5: MCPBA / CH₂Cl₂ / 1 h

6: CH₂Cl₂; diethyl ether

7: 88 percent / Et₃NHF / acetonitrile

8: DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

10: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) 10 min

11: 57 percent / LiCl, diisopropylethylamine / acetonitrile / 0.08 h

12: 17 percent / I₂ / hexane / 48 h / 23 °C

With dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide; iodine; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; triethylamine hydrofluoride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In diethyl ether; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00265a036

Reference yield:

: 88406-01-3
2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol

: 111649-67-3,118490-70-3,118490-71-4,118490-72-5,118490-75-8,118490-76-9,118490-77-0
(3aS,4S,5aR,6R,7S,9aR,9bS)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,4-trimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: Dowex-H⁺ / methanol

2: Et₃N, DMAP / CH₂Cl₂

3: TsOH

4: nBu₄NF, / tetrahydrofuran

5: DMSO, (COCl)2 / CH₂Cl₂; diethyl ether / 0.17 h / -78 °C

6: K₂CO₃ / methanol / 3 h / 23 °C

7: NaBH₄

8: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) 2 h

9: MCPBA / CH₂Cl₂ / 1 h

10: CH₂Cl₂; diethyl ether

11: DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

13: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) 10 min

15: benzene / 4 h / Heating

With dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; Dowex-H⁺; dimethylsulfide; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1021/jo00265a036