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

Base Information

• Chemical Name: (2S,3S,4E)-2--3-O-benzoyl-1-O-(tert-butyldimethylsilyl)-4-nonene-1,3-diol
• CAS No.: 149933-68-6
• Molecular Formula: C₃₅H₄₅NO₃Si
• Molecular Weight: 555.833
• Mol file: 149933-68-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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

There total 1 articles about (2S,3S,4E)-2--3-O-benzoyl-1-O-(tert-butyldimethylsilyl)-4-nonene-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: 69.0%

benzoyl chloride (98-88-4) + (2S,3S,4E)-2--1-O-(tert-butyldimethylsilyl)-4-nonene-1,3-diol (143428-52-8) → (2S,3S,4E)-2--3-O-benzoyl-1-O-(tert-butyldimethylsilyl)-4-nonene-1,3-diol (149933-68-6)

Guidance literature:

With pyridine; dmap; for 16h; Ambient temperature;

DOI:10.1021/jo00068a028

Reference yield: 63.0%

(2S,3S,4E)-2--3-O-benzoyl-1-O-(tert-butyldimethylsilyl)-4-nonene-1,3-diol (149933-68-6) → (2S,3S,4E)-2--1-O-benzoyl-4-nonene-1,3-diol (149933-70-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00068a028

Reference yield:

(2S,3S,4E)-2--3-O-benzoyl-1-O-(tert-butyldimethylsilyl)-4-nonene-1,3-diol (149933-68-6) → O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2S,3S,4E)-2--1-O-benzoyl-4-nonene-1,3-diol

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / TBAF / tetrahydrofuran / Ambient temperature

2: 60 percent / molecular sieves (4 Angstroem), silver triflate (AgOTfl) / CH₂Cl₂ / Ambient temperature

With 4 A molecular sieve; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00068a028

upstream raw materials:

benzoyl chloride

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

Downstream raw materials:

(2S,3S,4E)-2--1-O-benzoyl-4-nonene-1,3-diol