(3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

Base Information

Chemical Name:(3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol
CAS No.:118419-06-0
Molecular Formula:C₃₄H₄₈O₅Si
Molecular Weight:564.838
Hs Code.:

(3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

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Chemical Property of (3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

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Technology Process of (3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

There total 14 articles about (3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol 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:

: 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

: 118419-06-0
(3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

: 118437-02-8
(3aS,4S,5aS,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-5-hydroxy-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-6-carboxylic acid methyl ester

: 111649-68-4,118490-78-1
(3R,3aS,6S,6aS,9aR,9bS,9cS)-3-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6,8,8-trimethyl-3,3a,5a,6,6a,9a,9b,9c-octahydro-5,7,9-trioxa-cyclopenta[e]acenaphthylen-4-one

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 ℃;
DOI:10.1021/jo00265a036

Reference yield:

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

: 118419-06-0
(3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

Guidance literature:: Multi-step reaction with 13 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

13: NaBH₄ / ethanol / 0 °C

With dmap; sodium tetrahydroborate; 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; ethanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00265a036

Reference yield:

: (R)-2-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propionaldehyde

: 118419-06-0
(3aS,4S,5R,5aR,6S,7R,9aS,9bR)-7-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-2,2,4-trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxol-5-ol

Guidance literature:: Multi-step reaction with 9 steps

1: MCPBA / CH₂Cl₂ / 1 h

2: CH₂Cl₂; diethyl ether

3: 88 percent / Et₃NHF / acetonitrile

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

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

7: 57 percent / LiCl, diisopropylethylamine / acetonitrile / 0.08 h

8: 17 percent / I₂ / hexane / 48 h / 23 °C

9: NaBH₄ / ethanol / 0 °C

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; iodine; dimethyl sulfoxide; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In diethyl ether; ethanol; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo00265a036