(2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

Base Information

• Chemical Name: (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol
• CAS No.: 140479-38-5
• Molecular Formula: C₂₁H₃₆O₄Si
• Molecular Weight: 380.6

Synonyms:(2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

Chemical Property of (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

Chemical Property:

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Technology Process of (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

There total 4 articles about (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-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:

(R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde (133377-92-1) + allylmagnesium bromide (1730-25-2) → (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol (140479-38-5) + (2R,3S)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol (140479-43-2)

Guidance literature:

With zirconocene dichloride; In diethyl ether; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4039(91)80449-G

Reference yield:

(R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde (133377-92-1) → (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol (140479-38-5) + (2R,3S)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol (140479-43-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4039(91)80449-G

Reference yield:

(R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde (133377-92-1) + allyl bromide (106-95-6) → (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol (140479-38-5) + (2R,3S)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol (140479-43-2)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; Yield given. Yields of byproduct given; -15 deg C to r.t.;

DOI:10.1016/0040-4039(91)80449-G

upstream raw materials:

allyltributylstanane

(R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde

allyl bromide

allylmagnesium bromide

Downstream raw materials:

(2S,3R)-2-(((benzyloxy)methoxy)methyl)hex-5-ene-1,3-diol

(4R,5R)-cis-4-allyl-5-(((benzyloxy)methoxy)methyl)-2,2-dimethyl-1,3-dioxane

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