(2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol

Base Information

• Chemical Name: (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol
• CAS No.: 157037-45-1
• Molecular Formula: C₂₅H₃₅NO₂Si
• Molecular Weight: 409.644

Synonyms:(2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol

Chemical Property of (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol

Chemical Property:

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Technology Process of (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol

There total 2 articles about (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol 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: 70.0%

trans-2-propenyl bromide (590-15-8) + methyl O-tert-butyldimethylsilyl-N-(diphenylmethylene)-L-serinate (131472-75-8) → (R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol + (2S,3R,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol + (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol (157037-45-1)

Guidance literature:

With tert.-butyl lithium; triisobutylaluminum; diisobutylaluminium hydride; In hexane; dichloromethane; toluene;

DOI:10.1021/jo00095a039

Reference yield: 70.0%

(E)-propenyl lithium (6386-72-7,6524-17-0,29283-76-9) + methyl O-tert-butyldimethylsilyl-N-(diphenylmethylene)-L-serinate (131472-75-8) → (2S,3R,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol + (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol (157037-45-1) + (S)-2-(Benzhydrylidene-amino)-propan-1-ol

Guidance literature:

With i-Bu₂AlH*i-Bu₃Al; In toluene; at -78 - 0 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo9820115

Reference yield: 95.0%

acetic anhydride (108-24-7) + (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-hexene-1,3-diol (157037-45-1) → (2S,3S,4E)-3-Acetoxy-2--1-O-(tert-butyldimethylsilyl)-4-hexen-1-ol (157037-46-2)

Guidance literature:

With pyridine; dmap; for 24h; Ambient temperature;

DOI:10.1021/jo00095a039

upstream raw materials:

trans-2-propenyl bromide

methyl O-tert-butyldimethylsilyl-N-(diphenylmethylene)-L-serinate

(E)-propenyl lithium

Downstream raw materials:

(2S,3S,4E)-3-Acetoxy-2--1-O-(tert-butyldimethylsilyl)-4-hexen-1-ol

(2S,3R,4S,5R)-3,4,5-Triacetoxy-2--1-O-(tert-butyldimethylsilyl)hexan-1-ol

(2S,3R,4S,5R)-3,4,5-Triacetoxy-2-hexan-1-al

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