Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate

Base Information

• Chemical Name: Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate
• CAS No.: 92185-99-4
• Molecular Formula: C₃₇H₅₄O₄Si₂
• Molecular Weight: 619.004
• Mol file: 92185-99-4.mol

Synonyms:Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate

Chemical Property of Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate

There total 6 articles about Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate 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: 57.0%

Methyl (Z)-<(1R,2S,3R,5S)-2-tert-Butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-formylcyclopentyl>hept-5-enoate (135138-03-3) → Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate (92185-99-4)

Guidance literature:

DOI:10.1248/cpb.39.309

Reference yield:

(E)-5-[(1S,2R,3aS,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxy)-1-methanesulfonyloxy-octahydro-pentalen-2-yl]-pent-4-enoic acid methyl ester (92185-98-3) → Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate (92185-99-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; Yield given; Heating;

DOI:10.1248/cpb.37.586

Reference yield:

(E)-5-[(1S,2R,3aS,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-octahydro-pentalen-2-yl]-pent-4-enoic acid methyl ester (92185-97-2) → Methyl (1R,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octe-2-ene-3-γ-pentenoate (92185-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine

2: DBU / toluene / Heating

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In toluene;

DOI:10.1248/cpb.37.586

upstream raw materials:

Methyl (Z)-<(1R,2S,3R,5S)-2-tert-Butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-formylcyclopentyl>hept-5-enoate

(E)-5-[(1S,2R,3aS,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxy)-1-methanesulfonyloxy-octahydro-pentalen-2-yl]-pent-4-enoic acid methyl ester

(E)-5-[(1S,2R,3aS,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-octahydro-pentalen-2-yl]-pent-4-enoic acid methyl ester

methyl (Z)-7-<(1R,2S,3R)-2-tert-butyldimethylsilyloxymethyl-5-methylene-3-tetrahydropyranyloxycyclopentyl>hept-5-enoate

Downstream raw materials:

Methyl (1S,5S,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-tert-butyldiphenylsilyloxybicyclo<3.3.0>octane-E-Δ^3,δ-pentanoate