3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

Base Information

Chemical Name:3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester
CAS No.:150673-82-8
Molecular Formula:C₂₆H₃₂BrClO₇Si
Molecular Weight:599.978
Hs Code.:

Synonyms:3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

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Chemical Property of 3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

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Technology Process of 3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

There total 2 articles about 3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-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:

: 150650-39-8
1-O-(3-chlorobenzoyl)-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4,6-O-(phenylmethylene)-α-D-altropyranose

: 150673-82-8
3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

Guidance literature:: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); barium carbonate; In tetrachloromethane; for 0.75h; Heating;

Reference yield:

: 121702-70-3
tert-Butyl-dimethyl-((2R,4aR,8S,8aR)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-silane

: 150673-82-8
3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) MCPBA, 2.) Ca(OH)2 / 1.) CH₂Cl₂, 0 deg C, 45 min, 2.) CH₂Cl₂, 0 deg C, 20 min

2: NBS, BaCO₃, AIBN / CCl₄ / 0.75 h / Heating

With calcium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); 3-chloro-benzenecarboperoxoic acid; barium carbonate; In tetrachloromethane;

Reference yield:

: 150673-82-8
3-Chloro-benzoic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-pyran-2-yl ester

: Thioformic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3E)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester

Guidance literature:: Multi-step reaction with 10 steps

1: n-Bu₃SnH, AIBN / benzene / 1 h / Heating

2: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) CH₂Cl₂, from -78 to 25 deg C, 1 h

3: Zn(BH₄)2, NH₄Cl / diethyl ether / 0.33 h / 0 °C

4: PPh₃, diisopropyl azodicarboxylate (DIAD) / tetrahydrofuran / 0.5 h

5: 100 percent / 55percent aq. NH₂NH₂*H₂O / methanol / 0.25 h / 25 °C

6: PPTS / benzene / 3 h / 25 °C

7: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / -25 - 0 °C

8: 90 percent / DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

9: acetonitrile / 16 h / 25 °C

10: DIBAL / CH₂Cl₂ / 2 h / -78 °C

With 2,6-dimethylpyridine; zinc(II) tetrahydroborate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; ammonium chloride; hydrazine hydrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;