tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane
• CAS No.: 876173-62-5
• Molecular Formula: C₂₆H₃₅IO₄Si
• Molecular Weight: 566.552

Synonyms:tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane

There total 8 articles about tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane 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:

2-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-ethanol (876173-61-4) → tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane (876173-62-5)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1002/anie.200352868

Reference yield:

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone (99315-76-1) → tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane (876173-62-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / AlCl₃ / CH₂Cl₂ / 144 h / 60 °C

2: 98 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

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

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

5: 38.5 percent / Amberlyst 15; 3 Angstroem molecular sieves / diethyl ether / 10 h / 25 °C

6: NaBH₄ / methanol / 25 °C

7: 1.55 g / imidazole; PPh₃; I₂ / tetrahydrofuran / 25 °C

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; aluminium trichloride; N-methyl-2-indolinone; Amberlyst 15; 3 A molecular sieve; iodine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; tert-butyl alcohol; 1: Diels-Alder reaction;

DOI:10.1002/chem.200500513

Reference yield:

(+)-(1R,6S,7S)-7-diphenyl-t-butylsiloxymethyl-8-oxabicyclo-<4.3.0>non-3-en-9-one (99333-00-3) → tert-Butyl-[(2S,3S,3aR,5R,6aR)-3-(2-iodo-ethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-2-ylmethoxy]-diphenyl-silane (876173-62-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

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

3: 8.9 g / Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

4: 38.5 percent / Amberlyst 15; 3 Angstroem molecular sieves / diethyl ether / 10 h / 25 °C

5: NaBH₄ / methanol / 25 °C

6: 1.55 g / imidazole; PPh₃; I₂ / tetrahydrofuran / 25 °C

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; 3 A molecular sieve; iodine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1002/chem.200500513

upstream raw materials:

2-[(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-ethanol

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

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

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2S,3S,3aR,5R,6aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-carbaldehyde

tert-Butyl-((2S,3S,3aR,5R,6aR)-5-methoxy-3-vinyl-hexahydro-furo[2,3-b]furan-2-ylmethoxy)-diphenyl-silane

[(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

[(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

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