(-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

Base Information

Chemical Name:(-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate
CAS No.:289666-89-3
Molecular Formula:C₃₃H₄₄O₆Si
Molecular Weight:564.794
Hs Code.:

Synonyms:(-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

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Chemical Property of (-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

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Technology Process of (-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

There total 10 articles about (-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate 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: 89.0%

: 3282-30-2
pivaloyl chloride

: 289666-86-0
(-)-(2R,3S,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-1,2,4-pentanetriol

: 289666-89-3
(-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1021/ol052943c DOI:10.1021/jo060803q

Reference yield:

: (2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol

: 289666-89-3
(-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

Guidance literature:: Multi-step reaction with 3 steps

1: 61 percent / DMAP; Et₃N / CH₂Cl₂ / 10 h / 20 °C

2: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

3: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

With pyridine; dmap; water; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo060803q

Reference yield:

: 289666-88-2
(+)-(2R,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-pentol

: 289666-89-3
(-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

2: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

With pyridine; water; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo060803q