(3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one
• CAS No.: 130740-39-5
• Molecular Formula: C₂₅H₃₈O₆
• Molecular Weight: 434.573
• Mol file: 130740-39-5.mol

Synonyms:(3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one

Chemical Property of (3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one

There total 1 articles about (3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one 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: 75.0%

(E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol (130740-38-4,130852-78-7) → (3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one (130740-39-5)

Guidance literature:

With silver carbonate; In benzene; at 80 ℃;

DOI:10.1016/S0040-4039(00)97607-X

Reference yield:

(3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one (130740-39-5) → (E)-(1R,2S,4S,5R,6S,9R,10S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol (130740-43-1)

Guidance literature:

Multi-step reaction with 7 steps

1: HCl / H₂O

2: 2,6-lutidine

3: H₂ / Pd(OH)2

4: 2,6-lutidine

5: 97 percent / DIBAL-H / benzene / -78 °C

6: 1. sec-BuLi / 1. THF, -20 to 25 deg C; 2. THF; also in Et₂O

7: 1. MnO₂, 2. LiAlH₄ / 1. CH₂Cl₂, 2. Et₂O

With 2,6-dimethylpyridine; hydrogenchloride; manganese(IV) oxide; lithium aluminium tetrahydride; hydrogen; sec.-butyllithium; diisobutylaluminium hydride; palladium dihydroxide; In water; benzene;

DOI:10.1016/S0040-4039(00)97607-X

Reference yield:

(3S,5S)-5-((E)-(1S,2R,5S,6R)-7-Benzyloxy-1-methoxy-5-methoxymethoxy-2,4,6-trimethyl-hept-3-enyl)-3-methyl-dihydro-furan-2-one (130740-39-5) → (E)-(1R,2R,4R,5S,6R,9S,10R)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol (130740-43-1)

Guidance literature:

Multi-step reaction with 6 steps

1: HCl / H₂O

2: 2,6-lutidine

3: H₂ / Pd(OH)2

4: 2,6-lutidine

5: 97 percent / DIBAL-H / benzene / -78 °C

6: 1. sec-BuLi / 1. THF, -20 to 25 deg C; 2. THF; also in Et₂O

With 2,6-dimethylpyridine; hydrogenchloride; hydrogen; sec.-butyllithium; diisobutylaluminium hydride; palladium dihydroxide; In water; benzene;

DOI:10.1016/S0040-4039(00)97607-X

upstream raw materials:

(E)-(2S,4S,5R,6S,9R,10S)-11-Benzyloxy-5-methoxy-9-methoxymethoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol

Downstream raw materials:

(E)-(1R,2R,4R,5S,6R,9S,10R)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol

(E)-(1R,2S,4S,5R,6S,9R,10S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol