1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene

Base Information

• Chemical Name: 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene
• CAS No.: 911837-49-5
• Molecular Formula: C₄₇H₆₆O₅Si₂
• Molecular Weight: 767.209

Synonyms:1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene

Chemical Property of 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene

There total 9 articles about 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene 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: 95.0%

(2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-heptan-1-ol (911837-40-6) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene (911837-49-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.06.173

Reference yield:

(?)-(2S,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-ol (872369-16-9) → 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene (911837-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / Bu₂BOTf; Et₃N

2: 93 percent / NaBH₄ / tetrahydrofuran; H₂O

3: 95 percent / CSA / CH₂Cl₂

4: 95 percent / DIBAL-H / CH₂Cl₂ / 0 °C

5: 95 percent / 4-DMAP; pyridine / CH₂Cl₂; dimethylformamide

With pyridine; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Swern oxidation / 2: Evans aldol condensation;

DOI:10.1016/j.tetlet.2006.06.173

Reference yield:

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0) → 1-{(1R,2S,3S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-methyl-pentyloxymethyl}-4-methoxy-benzene (911837-49-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Bu₂BOTf; Et₃N

2: 93 percent / NaBH₄ / tetrahydrofuran; H₂O

3: 95 percent / CSA / CH₂Cl₂

4: 95 percent / DIBAL-H / CH₂Cl₂ / 0 °C

5: 95 percent / 4-DMAP; pyridine / CH₂Cl₂; dimethylformamide

With pyridine; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Evans aldol condensation;

DOI:10.1016/j.tetlet.2006.06.173

upstream raw materials:

(2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-heptan-1-ol

tert-butylchlorodiphenylsilane

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

(?)-(2S,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-ol

Downstream raw materials:

(R)-4-Benzyl-3-[(2R,3S,5S,6S,7R,8S)-5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,6-dimethyl-nonanoyl]-oxazolidin-2-one

5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-3,7-bis-(4-methoxy-benzyloxy)-2,6-dimethyl-nonan-1-ol

(4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-3,7-bis-(4-methoxy-benzyloxy)-2,6-dimethyl-nonanal

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