(1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one

Base Information

• Chemical Name: (1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one
• CAS No.: 481725-16-0
• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.326

Synonyms:(1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one

Chemical Property of (1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one

There total 2 articles about (1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-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: 78.0%

(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol (481725-15-9) → (1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-one (481725-16-0)

Guidance literature:

With tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/S0957-4166(02)00334-8

Reference yield:

(1S,2R,6R,7R)-4,10-Dioxa-tricyclo[5.2.1.02,6]dec-8-en-3-ol → (1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-one (481725-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

1.2: ClTi(O-i-Pr)3 / diethyl ether; pentane; hexane / -40 - 0 °C

1.3: 91 percent / tetrahydrofuran; diethyl ether; various solvents / 4.5 h / 0 - 20 °C

2.1: 78 percent / 4 Angstroem molecular sieves; 4-methoxymorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 5 h / 20 °C

With tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; tert.-butyl lithium; In diethyl ether; dichloromethane; pentane;

DOI:10.1016/S0957-4166(02)00334-8

Reference yield: 53.0%

(1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-one (481725-16-0) + 1-bromo-3-methoxy-4-propoxy-5-(2'-tert-butyldimethylsilyloxyethanesulfanyl)benzene (481725-11-5) → (1R,2S,3S,5S,6R,7S)-4,10-dioxa-3-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxy]-5-[(3',4',5')-trimethoxyphenyl]-tricyclo[5.2.1.02,6]dec-8-en-3-ol (481725-17-1)

Guidance literature:

1-bromo-3-methoxy-4-propoxy-5-(2'-tert-butyldimethylsilyloxyethanesulfanyl)benzene; With tert.-butyl lithium; In pentane; at -78 ℃; for 0.5h;

(1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(02)00334-8

upstream raw materials:

(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

Downstream raw materials:

(1R,2S,3S,5S,6R,7S)-4,10-dioxa-3-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxy]-5-[(3',4',5')-trimethoxyphenyl]-tricyclo[5.2.1.0^2,6]dec-8-en-3-ol

MK 287

(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfonyl)-4-propoxyphenyl]tetrahydrofuran

(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]-2,5-dihydrofuran

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