(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran
CAS No.:183805-39-2
Molecular Formula:C₃₀H₃₃BrO₄
Molecular Weight:537.494
Hs Code.:

Synonyms:(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

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Chemical Property of (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

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Technology Process of (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

There total 1 articles about (2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-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: 83.0%

: 81790-10-5
(2-bromoallyl)trimethylsilane

: 33639-74-6
(2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

: 183805-39-2
(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 15h;
DOI:10.1021/jo9621534

Reference yield: 72.0%

: 183805-45-0
N-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-2,2-dimethyl-8-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 183805-39-2
(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

: N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[2-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-but-3-enyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: With chromium dichloride; nickel dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; for 72h;
DOI:10.1021/ja960741t

Reference yield:

: 183805-39-2
(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

: N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-4-[(2S,3R,4S,6R)-4-hydroxy-6-hydroxymethyl-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 8 steps

1: 72 percent / CrCl₂, NiCl₂ / tetrahydrofuran; dimethylformamide / 72 h

2: 2,6-lutidene

3: 1.) 9-BBN, H₂O₂, 2.) Dess-Martin periodinane / 1.) THF, 0 deg C, 2.) CH₂Cl₂

4: tetrahydrofuran / -78 °C

5: TBAF / tetrahydrofuran

6: MCPBA / CH₂Cl₂

7: CSA / CH₂Cl₂

8: H₂ / Pd(OH)2/C / methanol

With 2,6-dimethylpyridine; chromium dichloride; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja960741t