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

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Chemical Name:(3S,4R,5S)-1α-(mesyloxy)-2,2-difluoro-3β-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5β-<(benzyloxy)methyl>-1,5-oxidopentane
CAS No.:143842-58-4
Molecular Formula:C₃₃H₄₀F₂O₈SSi
Molecular Weight:662.824
Hs Code.:

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

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

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

There total 10 articles about (3S,4R,5S)-1α-(mesyloxy)-2,2-difluoro-3β-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5β-<(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:

: 143842-35-7
(2R,3S)-1,3-dihydroxy-2-(1-hexynyl)-4-<(p-bromobenzyl)oxy>butane

: 143842-58-4
(3S,4R,5S)-1α-(mesyloxy)-2,2-difluoro-3β-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5β-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine, H₂ / Pd/BaSO₄ / 20 h / 760 Torr

2: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, RT, 90 min

3: 81 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 48 h / Ambient temperature

4: 1.) O₃, MeOH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 3 h

5: 47.2 percent / Zn, 1,2-dibromoethane, chlorotrimethylsilane / tetrahydrofuran / 3 h / Ambient temperature

6: AcOH / H₂O / 48 h / 65 °C

7: pyridine / 22 °C

8: NaBH₄ / methanol / 0.33 h / Ambient temperature

9: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; chloro-trimethyl-silane; dimethylsulfide; hydrogen; sodium hydride; ozone; acetic acid; ethylene dibromide; triethylamine; zinc; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00048a017

Reference yield:

: 124-63-0
methanesulfonyl chloride

: 143842-57-3
(3S,4R,5S)-1α-hydroxy-2,2-difluoro-3β-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5β-<(benzyloxy)methyl>-1,5-oxidopentane

: 143842-58-4
(3S,4R,5S)-1α-(mesyloxy)-2,2-difluoro-3β-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5β-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1021/ja00048a017

Reference yield:

: 143842-36-8
(2R,3S)-1,3-dihydroxy-2-(1-hexenyl)-4-(benzyloxy)butane

: 143842-58-4
(3S,4R,5S)-1α-(mesyloxy)-2,2-difluoro-3β-acetoxy-4α-<<(tert-butyldiphenylsilyl)oxy>methyl>-5β-<(benzyloxy)methyl>-1,5-oxidopentane

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, RT, 90 min

2: 81 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 48 h / Ambient temperature

3: 1.) O₃, MeOH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 3 h

4: 47.2 percent / Zn, 1,2-dibromoethane, chlorotrimethylsilane / tetrahydrofuran / 3 h / Ambient temperature

5: AcOH / H₂O / 48 h / 65 °C

6: pyridine / 22 °C

7: NaBH₄ / methanol / 0.33 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; chloro-trimethyl-silane; dimethylsulfide; sodium hydride; ozone; acetic acid; ethylene dibromide; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00048a017