(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran
CAS No.:190188-72-8
Molecular Formula:C₂₇H₃₆O₄
Molecular Weight:424.58
Hs Code.:

Synonyms:(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

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Chemical Property of (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

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Technology Process of (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

There total 6 articles about (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran 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: 84.0%

: 100-39-0
benzyl bromide

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

: 190188-72-8
(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; 1) 0 deg C, 15 min, 2) 0 deg C -> room temperature; room temperature, 16 h;
DOI:10.1016/S0040-4020(97)00282-2

Reference yield:

: 100-39-0
benzyl bromide

: 190188-72-8
(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 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: 39 percent / SeO₂, THBP / CH₂Cl₂ / 72 h / Ambient temperature

4: 84 percent / 1) NaH, nBu₄NI / dimethylformamide / 1) 0 deg C, 15 min, 2) 0 deg C -> room temperature; room temperature, 16 h

With selenium(IV) oxide; N,N,N,N,-tetramethylethylenediamine; tetra-(n-butyl)ammonium iodide; 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

: 190188-72-8
(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 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: 39 percent / SeO₂, THBP / CH₂Cl₂ / 72 h / Ambient temperature

5: 84 percent / 1) NaH, nBu₄NI / dimethylformamide / 1) 0 deg C, 15 min, 2) 0 deg C -> room temperature; room temperature, 16 h

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