(-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

Base Information

Chemical Name:(-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate
CAS No.:471282-14-1
Molecular Formula:C₂₁H₂₄O₇S₂
Molecular Weight:452.549
Hs Code.:

Synonyms:(-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

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Technology Process of (-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

There total 9 articles about (-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate 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: 68.0%

: 98-59-9
p-toluenesulfonyl chloride

: 2-Benzenesulfonyl-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

: 471282-15-2
(2R,3S,4R)-2-benzenesulfonylmethyl-3,4-isopropylidenedioxy-tetrahydrofuran

: 471282-13-0
(2S,3S,4R)-2-benzenesulfonylmethyl-3,4-isopropylidenedioxy-tetrahydrofuran

: 471282-14-1
(-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

: (2R,3S,4Z)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

Guidance literature:: 2-Benzenesulfonyl-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.666667h;

p-toluenesulfonyl chloride; In tetrahydrofuran; at -78 ℃; for 0.25h;

Reference yield: 60.0%

: 98-59-9
p-toluenesulfonyl chloride

: 471282-13-0
(2S,3S,4R)-2-benzenesulfonylmethyl-3,4-isopropylidenedioxy-tetrahydrofuran

: 471282-15-2
(2R,3S,4R)-2-benzenesulfonylmethyl-3,4-isopropylidenedioxy-tetrahydrofuran

: 471282-14-1
(-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/S0957-4166(02)00160-X

Reference yield:

: 219926-67-7
(2E,4E)-5-Phenylsulfonylpenta-2,4-dien-1-ol

: 471282-14-1
(-)-(2R,3S,4E)-5-benzenesulfonyl-2,3-iso-propylidene-dioxypent-4-en-1-yl-tosylate

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / L-(+)-DET; Ti(i-PrO)4; TBHP / CH₂Cl₂; decane / 48 h / 20 °C

2: 95 percent / pyridine / 0.5 h

3: 80 percent / AlCl₃ / 24 h

4: 90 percent / Na₂CO₃ / methanol / 2 h

5: 60 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; aluminium trichloride; diethyl (2R,3R)-tartrate; sodium carbonate; In tetrahydrofuran; methanol; decane; dichloromethane; 1: Sharpless epoxidation;
DOI:10.1016/S0957-4166(02)00160-X