(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

Base Information

• Chemical Name: (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
• CAS No.: 82849-09-0
• Molecular Formula: C₃₈H₇₂O₇Si₂
• Molecular Weight: 697.156

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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:

(2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol (82849-08-9) + 2,2-dimethoxy-propane (77-76-9) → (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 (82849-09-0)

Guidance literature:

With sulfuric acid; In acetone; at 0 ℃;

DOI:10.1021/ja00384a063

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (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 (82849-09-0)

Guidance literature:

Multi-step reaction with 4 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

With 2,6-dimethylpyridine; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1021/ja00384a063

Reference yield:

(4S,5R,6S,7S)-9-Benzyloxy-5-hydroxy-7-methoxy-4,6-dimethyl-nonan-3-one (82849-05-6) → (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 (82849-09-0)

Guidance literature:

Multi-step reaction with 4 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

With 2,6-dimethylpyridine; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; sulfuric acid; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1021/ja00384a063

upstream raw materials:

(2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol

2,2-dimethoxy-propane

t-butyldimethylsiyl triflate

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

Downstream raw materials:

(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

Trifluoro-acetic acid (1R,2R,3S)-3-methoxy-2-methyl-5-(toluene-4-sulfonyloxy)-1-((R)-1-{(4R,5R,6S)-2,2,5-trimethyl-6-[(S)-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-[1,3]dioxan-4-yl}-ethyl)-pentyl ester

(S)-6-[(4S,5R,6R)-6-((1R,2R,3R,4S)-6-Benzyloxy-4-methoxy-1,3-dimethyl-2-trimethylsilanyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-hydroxy-2-methyl-3-oxo-heptanoic acid benzyl ester

(R)-2-[(4R,5S,6R)-6-((1R,2R,3R,4S)-6-Benzyloxy-4-methoxy-1,3-dimethyl-2-trimethylsilanyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propionaldehyde

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