(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

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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol
• CAS No.: 865362-33-0
• Molecular Formula: C₃₆H₅₂O₉SSi
• Molecular Weight: 688.955
• Mol file: 865362-33-0.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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

There total 8 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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol 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: 99.0%

(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) → (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 (865362-33-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; at 20 ℃; for 1h;

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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol (865362-33-0)

Guidance literature:

Multi-step reaction with 5 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

5.1: 99 percent / TsOH*H₂O / methanol; CH₂Cl₂ / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium tert-butylate; toluene-4-sulfonic acid; 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-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol (865362-33-0)

Guidance literature:

Multi-step reaction with 3 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

3: 99 percent / TsOH*H₂O / methanol; CH₂Cl₂ / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ol051679k

upstream 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-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

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

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

chloromethyl phenyl sulfoxide

Downstream raw materials:

(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