(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

Base Information

Chemical Name:(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol
CAS No.:868593-37-7
Molecular Formula:C₂₀H₃₆O₅Si
Molecular Weight:384.588
Hs Code.:

Synonyms:(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

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Chemical Property of (S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

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Technology Process of (S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

There total 13 articles about (S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-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:

: 868593-30-0
(1S,4R,6R)-4-Methoxymethoxy-6-methoxymethyl-cyclohex-2-enol

: 868593-37-7
(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: KH / tetrahydrofuran / 20 °C

1.2: 62 percent / BuLi / -78 - -40 °C

2.1: 90 percent / Dess-Martin reagent

3.1: tetrahydrofuran / -78 °C

With potassium hydride; Dess-Martin periodane; In tetrahydrofuran; 1.2: Wittig-Still rearrangement / 2.1: Dess-Martin oxidation;
DOI:10.1055/s-2005-872222

Reference yield:

: 868593-32-2
((1S,4S,6R)-6-Methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-methanol

: 868593-37-7
(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / Dess-Martin reagent

2: tetrahydrofuran / -78 °C

With Dess-Martin periodane; In tetrahydrofuran; 1: Dess-Martin oxidation;
DOI:10.1055/s-2005-872222

Reference yield:

: 868593-28-6
tert-Butyl-((1S,4R,6R)-4-methoxymethoxy-6-methoxymethyl-cyclohex-2-enyloxy)-dimethyl-silane

: 868593-37-7
(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,4S,6R)-6-methoxymethoxy-4-methoxymethyl-cyclohex-2-enyl)-but-2-yn-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / TBAF / tetrahydrofuran / 20 °C

2.1: KH / tetrahydrofuran / 20 °C

2.2: 62 percent / BuLi / -78 - -40 °C

3.1: 90 percent / Dess-Martin reagent

4.1: tetrahydrofuran / -78 °C

With tetrabutyl ammonium fluoride; potassium hydride; Dess-Martin periodane; In tetrahydrofuran; 2.2: Wittig-Still rearrangement / 3.1: Dess-Martin oxidation;
DOI:10.1055/s-2005-872222