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

Base Information

Chemical Name:(1S,3R,4R,5R)-1β-Iodo-2,2-difluoro-3α-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane
CAS No.:151567-08-7
Molecular Formula:C₃₂H₃₇F₂IO₅Si
Molecular Weight:694.63
Hs Code.:

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

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

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

There total 12 articles about (1S,3R,4R,5R)-1β-Iodo-2,2-difluoro-3α-acetoxy-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: 37.0%

: 151567-07-6
(1R,3R,4R,5R)-1α-(Mesyloxy)-2,2-difluoro-3α-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

: 151567-08-7
(1S,3R,4R,5R)-1β-Iodo-2,2-difluoro-3α-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: With sodium iodide; In N,N-dimethyl-formamide; at 50 ℃; for 12h;
DOI:10.1021/jo00073a035

Reference yield:

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

: 151567-08-7
(1S,3R,4R,5R)-1β-Iodo-2,2-difluoro-3α-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: Multi-step reaction with 11 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

9: NaHCO₃ / H₂O; methanol / 2 h / Ambient temperature

10: pyridine / CH₂Cl₂ / 19 °C

11: 37 percent / NaI / dimethylformamide / 12 h / 50 °C

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

Reference yield:

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

: 151567-08-7
(1S,3R,4R,5R)-1β-Iodo-2,2-difluoro-3α-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5α-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: Multi-step reaction with 9 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

7: NaHCO₃ / H₂O; methanol / 2 h / Ambient temperature

8: pyridine / CH₂Cl₂ / 19 °C

9: 37 percent / NaI / dimethylformamide / 12 h / 50 °C

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