(4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Base Information

• Chemical Name: (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene
• CAS No.: 865362-16-9
• Molecular Formula: C₄₂H₆₆O₉SSi₂
• Molecular Weight: 803.218
• Mol file: 865362-16-9.mol

Synonyms:(4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Chemical Property of (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

There total 7 articles about (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene 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: 89.0%

(2S,3S)-2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxirane + Trifluoro-methanesulfonic acid (4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-ylmethyl ester (865362-14-7) → (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene (865362-16-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.5h;

DOI:10.1021/ol051679k

Reference yield:

(E)-5-((4-methoxybenzyl)oxy)-4-methylpent-3-enal → (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene (865362-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 79 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 82 percent / t-BuOK / CH₂Cl₂; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

3.1: 69 percent / magnesium monoperoxyphthalate hexahydrate / methanol / 2.5 h / 0 °C

4.1: 89 percent / HMPA; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -100 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium tert-butylate; magnesium monoperoxyphthalate hexahydrate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ol051679k

Reference yield:

2-Benzenesulfinyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxirane → (4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene (865362-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / magnesium monoperoxyphthalate hexahydrate / methanol / 2.5 h / 0 °C

2: 89 percent / HMPA; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -100 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; methanol; hexane;

DOI:10.1021/ol051679k

upstream raw materials:

Trifluoro-methanesulfonic acid (4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-ylmethyl ester

(E)-1-Benzenesulfinyl-1-chloro-6-(4-methoxy-benzyloxy)-5-methyl-hex-4-en-2-ol

chloromethyl phenyl sulfoxide

triethylsilyl trifluoromethyl sulfonate

Downstream raw materials:

(4aR,6S,7R,8aS)-6-{2-Benzenesulfonyl-3-[(E)-4-(4-methoxy-benzyloxy)-3-methyl-but-2-enyl]-oxiranylmethyl}-2,2-di-tert-butyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

(E)-3-Bromo-1-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-7-hydroxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-7-(4-methoxy-benzyloxy)-6-methyl-hept-5-en-2-one