(S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

Base Information

Chemical Name:(S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol
CAS No.:190188-71-7
Molecular Formula:C₂₀H₃₀O₄
Molecular Weight:334.456
Hs Code.:

Synonyms:(S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

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Chemical Property of (S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

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Technology Process of (S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

There total 5 articles about (S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol 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: 39.0%

: 167901-80-6
tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-erythro-non-8-enopyranoside

: 190188-71-7
(S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

: 190188-70-6
(R)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

Guidance literature:: With selenium(IV) oxide; In dichloromethane; for 72h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00282-2

Reference yield:

: 100-39-0
benzyl bromide

: 190188-71-7
(S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / NaH / dimethylformamide / 0 deg C -> room temperature; room temperature, 2 h

2: 85 percent / TMEDA / diethyl ether / 16 h / Ambient temperature

3: 31 percent / SeO₂, THBP / CH₂Cl₂ / 72 h / Ambient temperature

With selenium(IV) oxide; N,N,N,N,-tetramethylethylenediamine; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(97)00282-2

Reference yield:

: 107108-67-8
tert-butyl 2,3-deoxy-α-D-glucopyranoside

: 190188-71-7
(S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / pyridine / 0 deg C -> room temperature; room temperature, 4 h

2: 90 percent / NaH / dimethylformamide / 0 deg C -> room temperature; room temperature, 2 h

3: 85 percent / TMEDA / diethyl ether / 16 h / Ambient temperature

4: 31 percent / SeO₂, THBP / CH₂Cl₂ / 72 h / Ambient temperature

With pyridine; selenium(IV) oxide; N,N,N,N,-tetramethylethylenediamine; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(97)00282-2