(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

Base Information

Chemical Name:(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane
CAS No.:151567-01-0
Molecular Formula:C₃₅H₄₈O₅SSi
Molecular Weight:608.915
Hs Code.:

Synonyms:(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

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Chemical Property of (2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

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Technology Process of (2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

There total 1 articles about (2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane 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: 90.0%

: 124-63-0
methanesulfonyl chloride

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

: 151567-01-0
(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

Guidance literature:: With pyridine; at 19 ℃;
DOI:10.1021/jo00073a035

Reference yield:

: 151567-01-0
(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

: 151567-09-8
(1R,3R,4R,5R)-4α-(Hydroxymethyl)-5α-<(benzyloxy)methyl>-7,7-difluoro-2,6-dioxa<3.1.1>bicycloheptane

Guidance literature:: Multi-step reaction with 11 steps

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

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

3: 100 percent / pyridine / 12 h / Ambient temperature

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

5: K₂CO₃ / methanol / 1 h / 20 °C

6: NaBH₄ / methanol / 0.33 h / -40 °C

7: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

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

9: pyridine / CH₂Cl₂ / 19 °C

10: 37 percent / NaI / dimethylformamide / 12 h / 50 °C

11: K₂CO₃ / methanol; H₂O / 12 h / Ambient temperature

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:

: 151567-01-0
(2R,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-(1-heptenyl)-3-(mesyloxy)-4-(benzyloxy)butane

: 151567-10-1
(1R,3R,4R,5R)-4α-<<(Methanesulfonyl)oxy>methyl>-5α-<(benzyloxy)methyl>-7,7-difluoro-2,6-dioxa<3.1.1>bicycloheptane

Guidance literature:: Multi-step reaction with 12 steps

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

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

3: 100 percent / pyridine / 12 h / Ambient temperature

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

5: K₂CO₃ / methanol / 1 h / 20 °C

6: NaBH₄ / methanol / 0.33 h / -40 °C

7: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

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

9: pyridine / CH₂Cl₂ / 19 °C

10: 37 percent / NaI / dimethylformamide / 12 h / 50 °C

11: K₂CO₃ / methanol; H₂O / 12 h / Ambient temperature

12: 94 percent / pyridine / 1 h / 0 °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