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

Base Information

• Chemical Name: (3R,4S,5R,6R,7R)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-p-methoxybenzyloxy-3,5,7-trimethylnonan-8-al
• CAS No.: 203063-97-2
• Molecular Formula: C₃₁H₅₈O₅Si₂
• Molecular Weight: 566.97
• Mol file: 203063-97-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (3R,4S,5R,6R,7R)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-p-methoxybenzyloxy-3,5,7-trimethylnonan-8-al 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: 79.0%

(3S,4S,5R,6S,7R)-6,9-di-[(tert-butyldimethylsilyl)oxy]-4-p-methoxybenzyloxy-3,5,7-trimethylnon-1-ene (203063-96-1) → (3R,4S,5R,6R,7R)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-p-methoxybenzyloxy-3,5,7-trimethylnonan-8-al (203063-97-2)

Guidance literature:

With ozone; In methanol; dichloromethane;

DOI:10.1039/a707251a

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3R,4S,5R,6R,7R)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-p-methoxybenzyloxy-3,5,7-trimethylnonan-8-al (203063-97-2)

Guidance literature:

Multi-step reaction with 11 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

11: 79 percent / O₃ / methanol; CH₂Cl₂

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) → (3R,4S,5R,6R,7R)-1,4-di-[(tert-butyldimethylsilyl)oxy]-6-p-methoxybenzyloxy-3,5,7-trimethylnonan-8-al (203063-97-2)

Guidance literature:

Multi-step reaction with 9 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

9: 79 percent / O₃ / methanol; CH₂Cl₂

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:

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

t-butyldimethylsiyl triflate

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

(3R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-3,5-(dimethyl)hept-6-en-1-al

Downstream raw materials:

C₈₁H₁₅₃IO₁₂Si₅

rutamycin B

C₇₅H₁₃₉IO₁₂Si₄