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

Base Information

Chemical Name:1-O-(3-chlorobenzoyl)-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4,6-O-(phenylmethylene)-α-D-altropyranose
CAS No.:150650-39-8
Molecular Formula:C₂₆H₃₃ClO₇Si
Molecular Weight:521.082
Hs Code.:

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

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Chemical Property of 1-O-(3-chlorobenzoyl)-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4,6-O-(phenylmethylene)-α-D-altropyranose

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Technology Process of 1-O-(3-chlorobenzoyl)-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4,6-O-(phenylmethylene)-α-D-altropyranose

There total 1 articles about 1-O-(3-chlorobenzoyl)-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4,6-O-(phenylmethylene)-α-D-altropyranose 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:

: 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

: 535-80-8
3-chlorobenzoate

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

Guidance literature:: With calcium hydroxide; 3-chloro-benzenecarboperoxoic acid; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 45 min, 2.) CH₂Cl₂, 0 deg C, 20 min;

Reference yield:

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

: phenylmethyl 6-deoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-2-O-(phenylmethyl)-α-D-xylo-hexopyranosid-4-ulose O-<2,6-dideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-S-(1H-imidazol-1-ylcarbonyl)-4-thio-β-D-erythro-hex-3-enopyranosyl>oxime

Guidance literature:: Multi-step reaction with 10 steps

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

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

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

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

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

6: 100 percent / 55percent aq. NH₂NH₂*H₂O / methanol / 0.25 h / 25 °C

7: PPTS / benzene / 3 h / 25 °C

8: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / -25 - 0 °C

9: 90 percent / DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

10: acetonitrile / 16 h / 25 °C

With 2,6-dimethylpyridine; N-Bromosuccinimide; 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; barium carbonate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; acetonitrile; benzene;

Reference yield:

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

: phenylmethyl 6-deoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-2-O-(phenylmethyl)-α-D-xylo-hexopyranosid-4-ulose O-<2,6-dideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-S-(2,4,6-trimethylbenzoyl)-4-thio-β-D-erythro-hex-3-enopyranosyl>oxime

Guidance literature:: Multi-step reaction with 12 steps

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

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

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

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

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

6: 100 percent / 55percent aq. NH₂NH₂*H₂O / methanol / 0.25 h / 25 °C

7: PPTS / benzene / 3 h / 25 °C

8: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / -25 - 0 °C

9: 90 percent / DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

10: acetonitrile / 16 h / 25 °C

11: DIBAL / CH₂Cl₂ / 2 h / -78 °C

12: Et₃N, DMAP / CH₂Cl₂ / 12 h / 25 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; 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; barium carbonate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; acetonitrile; benzene;