(1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Base Information

Chemical Name:(1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane
CAS No.:151567-05-4
Molecular Formula:C₃₄H₄₀F₂O₇Si
Molecular Weight:626.77
Hs Code.:

Synonyms:(1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

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Chemical Property of (1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

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Technology Process of (1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

There total 9 articles about (1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane 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: 95.0%

: 108-24-7
acetic anhydride

: 151567-03-2
(3R,4R,5R)-1-Hydroxy-2,2-difluoro-3α-hydroxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

: 151567-05-4
(1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: With pyridine; In dichloromethane; Ambient temperature;
DOI:10.1021/jo00073a035

Reference yield:

: 143842-37-9
(2S,3S)-1-<(tert-butyldiphenylsilyl)oxy>-2-(1-hexenyl)-3-hydroxy-4-(benzyloxy)butane

: 151567-05-4
(1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / pyridine / 19 °C

2: 1.) O₃, MeOH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

3: Zn / tetrahydrofuran / 0.5 h / 0 - 10 °C

4: 100 percent / pyridine / 12 h / Ambient temperature

5: CsOAc / 1,2-dimethoxy-ethane / 22 h / Heating

6: K₂CO₃ / methanol / 1 h / 20 °C

7: NaBH₄ / methanol / 0.33 h / -40 °C

8: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; methanol; sodium tetrahydroborate; dimethylsulfide; cesium acetate; potassium carbonate; ozone; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jo00073a035

Reference yield:

: 151567-18-9
(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-formyl-3-(mesyloxy)-4-(benzyloxy)butane

: 151567-05-4
(1R,3R,4R,5R)-1α,3α-Diacetoxy-2,2-difluoro-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: Multi-step reaction with 6 steps

1: Zn / tetrahydrofuran / 0.5 h / 0 - 10 °C

2: 100 percent / pyridine / 12 h / Ambient temperature

3: CsOAc / 1,2-dimethoxy-ethane / 22 h / Heating

4: K₂CO₃ / methanol / 1 h / 20 °C

5: NaBH₄ / methanol / 0.33 h / -40 °C

6: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; sodium tetrahydroborate; cesium acetate; potassium carbonate; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jo00073a035