(3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate

Base Information

• Chemical Name: (3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate
• CAS No.: 478131-76-9
• Molecular Formula: C₃₀H₄₄O₄Si
• Molecular Weight: 496.762

Synonyms:(3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate

Chemical Property of (3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate

Chemical Property:

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Technology Process of (3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate

There total 2 articles about (3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate 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:

D-1,2,5,6-O-(3-pentylidene)-mannitol → (3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate (478131-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KHCO₃; KIO₄ / H₂O; tetrahydrofuran / 5 h / 25 °C

1.2: 54 percent / i-Pr₂NEt; LiCl / acetonitrile / 1.5 h / 25 °C

2.1: 82 percent / Me₂Zn; Me₂CuLi*LiCN / tetrahydrofuran; diethyl ether; toluene / 2.5 h / -78 °C

With potassium metaperiodate; dimethyl zinc(II); potassium hydrogencarbonate; dilithium dimethylcyanocuprate; In tetrahydrofuran; diethyl ether; water; toluene;

DOI:10.1021/ja027335w

Reference yield:

L-mannitol (643-01-6) → (3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate (478131-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: camphorsulfonic acid / dimethylformamide / 5 h / 40 °C

2.1: KHCO₃; KIO₄ / H₂O; tetrahydrofuran / 5 h / 25 °C

2.2: 54 percent / i-Pr₂NEt; LiCl / acetonitrile / 1.5 h / 25 °C

3.1: 82 percent / Me₂Zn; Me₂CuLi*LiCN / tetrahydrofuran; diethyl ether; toluene / 2.5 h / -78 °C

With potassium metaperiodate; camphor-10-sulfonic acid; dimethyl zinc(II); potassium hydrogencarbonate; dilithium dimethylcyanocuprate; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja027335w

Reference yield:

(3S,4R)-3-(dimesitylsilyl)-4,5-O-(3-pentilidene)-4,5-dihydroxypentanoate (478131-76-9) → (R)-3-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-5-ethoxy-2,2-bis-(2,4,6-trimethyl-phenyl)-[1,2]oxasilolane + (3S,4R)-1-oxa-3-(1,2,-O-(3-pentilidene)-1,2-hydroxyethyl)-5-ethoxy-2,2-(dimesityl)silacyclopentane

Guidance literature:

With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 0 - 25 ℃; for 3h; Title compound not separated from byproducts.;

DOI:10.1021/ja027335w

upstream raw materials:

L-mannitol

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