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

Base Information

• Chemical Name: [(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((3aS,7aS)-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanone
• CAS No.: 678160-10-6
• Molecular Formula: C₃₇H₅₀O₅Si
• Molecular Weight: 602.886

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 26 articles about [(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((3aS,7aS)-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanone 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: 95.0%

[(2S,3R,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((3aS,7aS)-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol (678160-21-9) → [(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((3aS,7aS)-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanone (678160-10-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 10h;

DOI:10.1002/anie.200352868

Reference yield:

(+)-(1R,6S,7S)-7-diphenyl-t-butylsiloxymethyl-8-oxabicyclo-<4.3.0>non-3-en-9-one (99333-00-3) → [(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((3aS,7aS)-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanone (678160-10-6)

Guidance literature:

Multi-step reaction with 12 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

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

DOI:10.1002/chem.200500513

Reference yield:

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone (99315-76-1) → [(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-((3aS,7aS)-4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanone (678160-10-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 85 percent / AlCl₃ / CH₂Cl₂ / 144 h / 60 °C

2.1: 98 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

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

4.1: 8.9 g / Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

5.1: 38.5 percent / Amberlyst 15; 3 Angstroem molecular sieves / diethyl ether / 10 h / 25 °C

6.1: NaBH₄ / methanol / 25 °C

7.1: 1.55 g / imidazole; PPh₃; I₂ / tetrahydrofuran / 25 °C

8.1: 95 percent / NaBH₄ / ethanol / 25 °C

9.1: 83 percent / aq. NaIO₄ / tetrahydrofuran; methanol / 0.5 h / 25 °C

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

11.1: 1.75 g / Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

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

12.2: 51 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

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

With pyridine; 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; aluminium trichloride; N-methyl-2-indolinone; Amberlyst 15; 3 A molecular sieve; iodine; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone; toluene; tert-butyl alcohol; pentane; 1.1: Diels-Alder reaction / 13.1: Dess-Martin oxidation;

DOI:10.1002/chem.200500513

upstream raw materials:

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

dithiocarbonic acid O-[3-(tert-butyl-diphenyl-silanyloxy)-3a,7,7-trimethyl-octahydro-inden-1-yl] ester S-methyl ester

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

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

Downstream raw materials:

[(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

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

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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