Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

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Chemical Name:Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester
CAS No.:113892-53-8
Molecular Formula:C₂₅H₃₄O₆Si
Molecular Weight:458.627
Hs Code.:

Synonyms:Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester 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: 96.0%

: 113892-52-7
Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester

: 113892-53-8
Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; dihydrogen peroxide; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1021/ja00220a035

Reference yield:

: 113892-49-2
Benzoic acid (Z)-4-furan-2-yl-4-hydroxy-2-oxo-but-3-enyl ester

: 113892-53-8
Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 3.6 g / diethyl ether / 1 h / 0 °C

2: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min

3: 1.) Dibal; 2.) DMF; 3.) BF₃*OEt₂; 4.) trifluoroacetic acid

4: ceric chloride heptahydrate, NaBH₄ / CH₂Cl₂; ethanol / 1 h / -78 °C

5: 90 percent / CSA / methanol; benzene / 3 h / 25 °C

6: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

7: 96 percent / H₂O₂, pyridine / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00220a035

Reference yield:

: 92622-30-5
Benzoic acid (Z)-4-furan-2-yl-4-methoxy-2-oxo-but-3-enyl ester

: 113892-53-8
Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-vinyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min

2: 1.) Dibal; 2.) DMF; 3.) BF₃*OEt₂; 4.) trifluoroacetic acid

3: ceric chloride heptahydrate, NaBH₄ / CH₂Cl₂; ethanol / 1 h / -78 °C

4: 90 percent / CSA / methanol; benzene / 3 h / 25 °C

5: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6: 96 percent / H₂O₂, pyridine / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00220a035