(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-ene

Base Information

• Chemical Name: (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-ene
• CAS No.: 481725-18-2
• Molecular Formula: C₃₅H₅₀O₈SSi
• Molecular Weight: 658.929

Synonyms:(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-ene

Chemical Property of (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-ene

Chemical Property:

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Technology Process of (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-ene

There total 12 articles about (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-ene 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: 75.0%

(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) → (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-ene (481725-18-2) + (1R,2S,3R,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-ene

Guidance literature:

With dichloro-acetic acid; sodium cyanoborohydride; In various solvent(s); at -25 ℃; for 0.5h;

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

Reference yield:

5-iodovaniline (5438-36-8) → (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-ene (481725-18-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / cesium carbonate / dimethylformamide / 2 h / 50 °C

2.1: 91 percent / 2-methyl-2-butene; aq. sodium chlorite; NaH₂PO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

3.1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 18 h / 20 °C

4.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl₃; AIBN / 0.08 h / Heating

5.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C

6.1: 92 percent / imidazole / dimethylformamide / 20 °C

7.1: t-BuLi / pentane / 0.5 h / -78 °C

7.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C

8.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 °C

With 1H-imidazole; dichloro-acetic acid; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; tert.-butyl lithium; 2-mercaptopyridine-1-oxide sodium salt; copper; sodium cyanoborohydride; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;

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

Reference yield:

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) → (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-ene (481725-18-2)

Guidance literature:

Multi-step reaction with 4 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

3.1: t-BuLi / pentane / 0.5 h / -78 °C

3.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C

4.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 °C

With dichloro-acetic acid; tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; tert.-butyl lithium; sodium cyanoborohydride; In diethyl ether; dichloromethane; pentane;

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

upstream 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

5-iodovaniline

1-bromo-3,4,5-trimethoxybenzene

3-methoxy-4-n-propyloxy-5-iodobenzaldehyde

Downstream raw materials:

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]tetrahydrofuran

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

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