(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

Base Information

Chemical Name:(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol
CAS No.:82849-10-3
Molecular Formula:C₂₆H₄₄O₆
Molecular Weight:452.632
Hs Code.:

Synonyms:(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

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Chemical Property of (2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

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Technology Process of (2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

There total 5 articles about (2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-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:

: 82849-09-0
(4R,5R,6S)-4-[(1R,2R,3R,4S)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,3-dimethyl-hexyl]-2,2,5-trimethyl-6-[(S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-[1,3]dioxane

: 82849-10-3
(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 40 ℃; for 36h;
DOI:10.1021/ja00384a063

Reference yield:

: 82849-05-6
(4S,5R,6S,7S)-9-Benzyloxy-5-hydroxy-7-methoxy-4,6-dimethyl-nonan-3-one

: 82849-10-3
(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C

3: diisobutylaluminium hydride / diethyl ether / -78 °C

4: conc. H₂SO₄ / acetone / 0 °C

5: n-Bu₄NF / tetrahydrofuran / 36 h / 40 °C

With 2,6-dimethylpyridine; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1021/ja00384a063

Reference yield:

: 82864-88-8
(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

: 82849-10-3
(2S,3R,4S,5S)-7-Benzyloxy-2-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-4-methyl-heptan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C

2: diisobutylaluminium hydride / diethyl ether / -78 °C

3: conc. H₂SO₄ / acetone / 0 °C

4: n-Bu₄NF / tetrahydrofuran / 36 h / 40 °C

With zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; acetone;
DOI:10.1021/ja00384a063