(3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene

Base Information

• Chemical Name: (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene
• CAS No.: 203063-96-1
• Molecular Formula: C₃₂H₆₀O₄Si₂
• Molecular Weight: 564.997
• Mol file: 203063-96-1.mol

Synonyms:(3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene

Chemical Property of (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene

There total 11 articles about (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene 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: 68.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (3R,4S,5R,6S,7S)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-3,5,7-trimethyl-non-8-ene (203063-95-0) → (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene (203063-96-1)

Guidance literature:

With trifluorormethanesulfonic acid; at -10 ℃;

DOI:10.1039/a707251a

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene (203063-96-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / Et₃N / CH₂Cl₂

2: 85 percent / NH₄F / methanol / Heating

3: 92 percent / pyridine

4: 94 percent / dimethylsulfoxide

5: 75 percent / DIBAL-H / toluene / -78 °C

6: 87 percent / NaBH₄ / propan-2-ol / 0 °C

7: 96 percent / imidazole / dimethylformamide

8: 94 percent / O₃ / CH₂Cl₂; methanol

9: 78 percent / 4A MS / toluene / -78 °C

10: 68 percent / CF₃SO₃H / -10 °C

With pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; trifluorormethanesulfonic acid; diisobutylaluminium hydride; ozone; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1039/a707251a

Reference yield:

(2R,3R,4R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-2,4-dimethylhex-5-ene (203063-88-1) → (3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene (203063-96-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / pyridine

2: 94 percent / dimethylsulfoxide

3: 75 percent / DIBAL-H / toluene / -78 °C

4: 87 percent / NaBH₄ / propan-2-ol / 0 °C

5: 96 percent / imidazole / dimethylformamide

6: 94 percent / O₃ / CH₂Cl₂; methanol

7: 78 percent / 4A MS / toluene / -78 °C

8: 68 percent / CF₃SO₃H / -10 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; trifluorormethanesulfonic acid; diisobutylaluminium hydride; ozone; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1039/a707251a

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

(3R,4S,5R,6S,7S)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-3,5,7-trimethyl-non-8-ene

t-butyldimethylsiyl triflate

(2R,3R,4R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-2,4-dimethylhex-5-ene

Downstream raw materials:

C₈₁H₁₅₃IO₁₂Si₅

C₇₅H₁₃₉IO₁₂Si₄

rutamycin B

(3R,4S,5R,6R,7R)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-p-methoxybenzyloxy-3,5,7-trimethylnonan-8-al