(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Base Information

Chemical Name:(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester
CAS No.:912542-29-1
Molecular Formula:C₃₀H₄₂O₅Si
Molecular Weight:510.746
Hs Code.:

Synonyms:(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

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Chemical Property of (1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

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Technology Process of (1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

There total 13 articles about (1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-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: 75.0%

: 67-56-1
methanol

: 901265-18-7
(1R,2S,5S)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2,5-dimethyl-cyclohex-3-enecarbaldehyde

: 912542-29-1
(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: methanol; (1R,2S,5S)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2,5-dimethyl-cyclohex-3-enecarbaldehyde; With potassium hydroxide; iodine; at 0 ℃; for 0.5h;

With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/jo061059c

Reference yield:

: 901266-80-6
2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxymethyl-2,5-dimethyl-cyclohex-3-enol

: 912542-29-1
(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 75 percent / DMSO; i-Pr₂NEt; SO₃*pyridine / CH₂Cl₂ / 0.25 h

2.1: KOH; I₂ / 0.5 h / 0 °C

2.2: 75 percent / PPTS / methanol / 2 h / 20 °C

With potassium hydroxide; pyridine-SO₃ complex; iodine; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo061059c

Reference yield:

: 912542-41-7
6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dimethyl-cyclohexa-1,4-dienecarbaldehyde

: 912542-29-1
(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2.1: 96 percent / VO(acac)2; t-BuOOH / CH₂Cl₂; decane / 0 - 23 °C

3.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 23 °C

4.1: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / 0 °C

5.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 1 h

6.1: 97 percent / n-Bu₃SnH; Et₃B; O₂ / toluene; hexane / 0.17 h

7.1: 90 percent / K₂CO₃ / methanol / 24 h

8.1: 85 percent / SO₃*pyridine; DMSO; i-Pr₂NEt₂ / CH₂Cl₂ / 0.25 h

9.1: KOH; I₂ / 0.5 h / 0 °C

9.2: 75 percent / PPTS / methanol / 2 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; potassium hydroxide; bis(acetylacetonate)oxovanadium; pyridine-SO₃ complex; triethyl borane; i-Pr₂NEt₂; boron trifluoride diethyl etherate; iodine; oxygen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; In methanol; decane; hexane; dichloromethane; toluene;
DOI:10.1021/jo061059c