((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

Base Information

Chemical Name:((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane
CAS No.:160860-78-6
Molecular Formula:C₄₄H₄₇BrO₅Si
Molecular Weight:763.844
Hs Code.:

Synonyms:((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

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Chemical Property of ((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

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Technology Process of ((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

There total 7 articles about ((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-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: 84.0%

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 160860-75-3
(1S,2R,3R,4S,5R,6R)-3-Bromo-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,6-diol

: 160860-78-6
((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

Guidance literature:: DOI:10.1021/jo00106a008

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 160860-78-6
((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: KHMDS / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) 0 deg C, 1 h

2: tetrahydrofuran / 6 h / -100 °C

3: 93 percent / 2 M aq. HCl / acetonitrile / 0 °C

4: 94 percent / NaBH₄ / ethanol / -78 °C

5: 79 percent / DMAP / tetrahydrofuran / 48 h / 22 °C

6: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) -78 deg C, 1 h; 22 deg C, 1 h

7: 81 percent / DIBAL-H / toluene / 1.) -78 deg C, 30 min, 2.) -20 deg C, 3.5 h

8: 84 percent

With hydrogenchloride; dmap; sodium tetrahydroborate; 2,3-dimercapto-succinic acid; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; In tetrahydrofuran; ethanol; toluene; acetonitrile;
DOI:10.1021/jo00106a008

Reference yield:

: 160860-70-8
(S)-1-[4-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-furan-3-yl]-2-(1-methoxy-1-methyl-ethyl)-pyrrolidine

: 160860-78-6
((1S,2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-7-oxa-bicyclo[2.2.1]hept-1-yloxy)-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 6 h / -100 °C

2: 93 percent / 2 M aq. HCl / acetonitrile / 0 °C

3: 94 percent / NaBH₄ / ethanol / -78 °C

4: 79 percent / DMAP / tetrahydrofuran / 48 h / 22 °C

5: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) -78 deg C, 1 h; 22 deg C, 1 h

6: 81 percent / DIBAL-H / toluene / 1.) -78 deg C, 30 min, 2.) -20 deg C, 3.5 h

7: 84 percent

With hydrogenchloride; dmap; sodium tetrahydroborate; 2,3-dimercapto-succinic acid; diisobutylaluminium hydride; ozone; In tetrahydrofuran; ethanol; toluene; acetonitrile;
DOI:10.1021/jo00106a008