{(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

Base Information

Chemical Name:{(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane
CAS No.:931095-15-7
Molecular Formula:C₃₂H₄₆O₅Si
Molecular Weight:538.8
Hs Code.:

Synonyms:{(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

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Chemical Property of {(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

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Technology Process of {(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

There total 3 articles about {(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane 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: 91.0%

: 931095-26-0
(1R)-1-[(1S,4S,5R,6R)-6-benzyloxy-5-methoxymethyl-4-triethylsilanyloxy-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-acetaldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 931095-15-7
{(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; for 0.0833333h; Heating;

(1R)-1-[(1S,4S,5R,6R)-6-benzyloxy-5-methoxymethyl-4-triethylsilanyloxy-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-acetaldehyde; In tetrahydrofuran; at 20 ℃; for 0.166667h;
DOI:10.1021/ol0630189

Reference yield:

: 931095-25-9
(1S)-1-[(1S,4S,5R,6R)-6-benzyloxy-5-methoxymethyl-4-triethylsilanyloxy-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-acetic acid methyl ester

: 931095-15-7
{(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

2.1: tBuOK / tetrahydrofuran / 0.08 h / Heating

2.2: 91 percent / tetrahydrofuran / 0.17 h / 20 °C

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; 2.2: Wittig olefination;
DOI:10.1021/ol0630189

Reference yield:

: (1S)-1-[(1S,4S,5R,6R)-6-benzyloxy-5-methoxymethyl-4-triethylsilanyloxy-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-acetic acid

: 931095-15-7
{(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyloxy}-triethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 180 mg / toluene; methanol; hexane / 0.17 h / 20 °C

2.1: 93 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

3.1: tBuOK / tetrahydrofuran / 0.08 h / Heating

3.2: 91 percent / tetrahydrofuran / 0.17 h / 20 °C

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 3.2: Wittig olefination;
DOI:10.1021/ol0630189