2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Base Information

• Chemical Name: 2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one
• CAS No.: 402571-19-1
• Molecular Formula: C₅₁H₈₈O₉Si₂
• Molecular Weight: 901.425
• Mol file: 402571-19-1.mol

Synonyms:

Chemical Property of 2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one

There total 1 articles about 2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-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:

di-tert-butylsilyl bis(trifluoromethanesulfonate) (85272-31-7) + (E)-2-methylpent-2-enal (623-36-9) + pentan-3-one (96-22-0) + (2S,3S,4R,5S,6S)-6-(6-Ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-triethylsilanyloxy-heptanal (402571-16-8) → 2-[(1S,2S,3R,4R,5R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one + 2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one (402571-19-1)

Guidance literature:

Multistep reaction.;

DOI:10.1021/ol017082w

Reference yield:

2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one (402571-19-1) → 2-[(1S,2S,3S,4S,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-2,6-dihydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; dichloromethane;

DOI:10.1021/ol017082w

Reference yield:

2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one (402571-19-1) → (4S,5S,6R,8R)-2-((3S,4S,5S,6S)-6-Ethyl-2,4-dihydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-8-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-nonane-3,7-dione (402571-20-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium p-toluenesulfonate / methanol; CH₂Cl₂

2: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂

3: 69 percent / HF*pyridine; pyridine / tetrahydrofuran

With pyridine; oxalyl dichloride; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation;

DOI:10.1021/ol017082w

upstream raw materials:

di-tert-butylsilyl bis(trifluoromethanesulfonate)

(E)-2-methylpent-2-enal

pentan-3-one

(2S,3S,4R,5S,6S)-6-(6-Ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-triethylsilanyloxy-heptanal

Downstream raw materials:

(4S,5S,6R,8R)-2-((3S,4S,5S,6S)-6-Ethyl-2,4-dihydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-8-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-nonane-3,7-dione