(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

Base Information

Chemical Name:(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
CAS No.:160860-75-3
Molecular Formula:C₂₃H₂₉BrO₅Si
Molecular Weight:493.47
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

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Useful:

Technology Process of (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

There total 7 articles about (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 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: 81.0%

: 160860-74-2
(1S,2R,4R,5R,6R)-6-Bromo-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-3-oxo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

: 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

Guidance literature:: With diisobutylaluminium hydride; In toluene; 1.) -78 deg C, 30 min, 2.) -20 deg C, 3.5 h;
DOI:10.1021/jo00106a008

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 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

Guidance literature:: Multi-step reaction with 7 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

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

: 160860-75-3
(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

Guidance literature:: Multi-step reaction with 6 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

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