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

Base Information

Chemical Name:[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol
CAS No.:876173-73-8
Molecular Formula:C₃₇H₅₂O₅Si
Molecular Weight:604.902
Hs Code.:

[2-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-<i>b</i>]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3<i>H</i>-inden-1-yl)-methanol

Synonyms:[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol

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Chemical Property of [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol

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Technology Process of [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol

There total 18 articles about [2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol 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: 54.0%

: 876173-72-7
2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-carbaldehyde

: 678159-97-2
(-)-(3aS,7aS)-3-iodo-3a,7,7-trimethyl-3a,4,5,6,7,7a-hexahydro-1H-indene

: 876173-73-8
[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol

Guidance literature:: (-)-(3aS,7aS)-3-iodo-3a,7,7-trimethyl-3a,4,5,6,7,7a-hexahydro-1H-indene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;

2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-carbaldehyde; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;
DOI:10.1002/chem.200500513

Reference yield:

: 876173-71-6
tert-butyl-(5-methoxy-3-vinyl-hexahydro-furo[2,3-b]furan-2-ylmethoxy)-diphenyl-silane

: 876173-73-8
[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 1.8 g / Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

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

3.2: 54 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

With pyridine; lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; tert.-butyl lithium; In tetrahydrofuran; dichloromethane; acetone; pentane;
DOI:10.1002/chem.200500513

Reference yield:

: 3-(tert-butyl-diphenyl-silanyloxy)-3a,7,7-trimethyl-octahydro-inden-1-ol

: 876173-73-8
[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-hexahydro-furo[2,3-b]furan-3-yl]-(4,4,7a-trimethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / 0 °C

1.2: tetrahydrofuran; hexane / 1.5 h / 0 °C

1.3: tetrahydrofuran; hexane / 1.5 h / 0 °C

2.1: 100 percent / n-Bu₃SnH; AIBN / toluene / 0.33 h / 120 °C

3.1: 99 percent / TBAF / tetrahydrofuran / 8 h / 25 °C

4.1: 92 percent / PCC; Celite / CH₂Cl₂ / 12 h / 25 °C

5.1: 99 percent / N₂H₄*H₂O; Et₃N / ethanol / 12 °C / Heating

6.1: 62 percent / DBU; I₂ / diethyl ether / 0.25 h / 25 °C

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

7.2: 54 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); Celite; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; pentane; 2.1: Barton-McCombie radical deoxygenation;
DOI:10.1002/chem.200500513