1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

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Chemical Name:1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol
CAS No.:678160-22-0
Molecular Formula:C₃₈H₅₆O₅Si
Molecular Weight:620.945
Hs Code.:

1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

Synonyms:1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

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Chemical Property of 1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

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Technology Process of 1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

There total 38 articles about 1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol 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%

: 917-54-4
methyllithium

: 678160-11-7
[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-methanone

: 678160-22-0
1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

Guidance literature:: In tetrahydrofuran; 1,2-dimethoxyethane; at 0 ℃; for 0.5h;
DOI:10.1002/anie.200352868

Reference yield:

: 678160-18-4
(+)-(1S,3aS,7aS)-4,4,7a-trimethyloctahydro-1H-inden-1-ol

: 678160-22-0
1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / PCC; Celite / CH₂Cl₂ / 12 h / 25 °C

2.1: 99 percent / N₂H₄*H₂O; Et₃N / ethanol / 12 °C / Heating

3.1: 62 percent / DBU; I₂ / diethyl ether / 0.25 h / 25 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

4.2: 54 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

5.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

6.1: 75 percent / H₂ / Pd/C / methanol / 16 h / 25 °C

7.1: 75 percent / tetrahydrofuran; 1,2-dimethoxy-ethane; diethyl ether / 0.5 h / 0 °C

With Celite; hydrogen; iodine; tert.-butyl lithium; Dess-Martin periodane; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; pentane; 5.1: Dess-Martin oxidation;
DOI:10.1002/chem.200500513

Reference yield:

: 99333-00-3
(+)-(1R,6S,7S)-7-diphenyl-t-butylsiloxymethyl-8-oxabicyclo-<4.3.0>non-3-en-9-one

: 678160-22-0
1-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-1-((1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl)-ethanol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 98 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2.1: aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 10 h / 25 °C

3.1: 8.9 g / Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

4.1: 38.5 percent / Amberlyst 15; 3 Angstroem molecular sieves / diethyl ether / 10 h / 25 °C

5.1: NaBH₄ / methanol / 25 °C

6.1: 1.55 g / imidazole; PPh₃; I₂ / tetrahydrofuran / 25 °C

7.1: 95 percent / NaBH₄ / ethanol / 25 °C

8.1: 83 percent / aq. NaIO₄ / tetrahydrofuran; methanol / 0.5 h / 25 °C

9.1: aq. OsO₄; NMO; pyridine / acetone / 10 h / 25 °C

10.1: 1.75 g / Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

11.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

11.2: 51 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

12.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

13.1: 83 percent / H₂ / Pd/C / methanol / 16 h / 25 °C

14.1: 75 percent / tetrahydrofuran; 1,2-dimethoxy-ethane; diethyl ether / 0.5 h / 0 °C

With pyridine; 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; 3 A molecular sieve; hydrogen; iodine; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; acetone; toluene; tert-butyl alcohol; pentane; 12.1: Dess-Martin oxidation;
DOI:10.1002/chem.200500513