<2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran

Base Information

• Chemical Name: <2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran
• CAS No.: 147646-10-4
• Molecular Formula: C₁₉H₂₇N₃O₇S
• Molecular Weight: 441.505

Synonyms:<2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran

Chemical Property of <2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran

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Technology Process of <2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran

There total 10 articles about <2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran 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: 94.0%

p-toluenesulfonyl chloride (98-59-9) + <2S-<2α(2R*,4R*),3α,6α>>-2-<1-(Hydroxymethyl)-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-08-0) → <2S-<2α(2R*,4R*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-10-4)

Guidance literature:

With dmap; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00062a035

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → <2S-<2α(2R*,4R*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-10-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1 h, then r.t., 4 h

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) r.t., 1 h

3: 1.) n-BuLi, 2.) ZnBr₂ / 1.) THF, -10 deg C, 2 h, 2.) -20 to -25 deg C, 4 h

4: 81 percent / t-BuOOH, VO(acac)2 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 1.) 0 deg C, 1 h, 2.) r.t., 3.5 h

5: Ag₂O / 58 h / Ambient temperature

6: 92 percent / K-Selectride, EtOH / tetrahydrofuran / 2 h / -100 °C

7: 84 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) r.t., 3.5 h

8: 87 percent / NaN₃ / dimethylformamide / 15 h / 105 °C

9: 92 percent / n-Bu₄NF / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 1 h

10: 94 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; n-butyllithium; sodium azide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; ethanol; tetrabutyl ammonium fluoride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; triethylamine; silver(l) oxide; zinc dibromide; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00062a035

Reference yield:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol (136032-73-0,127251-09-6) → <2S-<2α(2R*,4R*),3α,6α>>-2-<1-<<(Tolylsulfonyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-10-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) r.t., 1 h

2: 1.) n-BuLi, 2.) ZnBr₂ / 1.) THF, -10 deg C, 2 h, 2.) -20 to -25 deg C, 4 h

3: 81 percent / t-BuOOH, VO(acac)2 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 1.) 0 deg C, 1 h, 2.) r.t., 3.5 h

4: Ag₂O / 58 h / Ambient temperature

5: 92 percent / K-Selectride, EtOH / tetrahydrofuran / 2 h / -100 °C

6: 84 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) r.t., 3.5 h

7: 87 percent / NaN₃ / dimethylformamide / 15 h / 105 °C

8: 92 percent / n-Bu₄NF / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 1 h

9: 94 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; n-butyllithium; sodium azide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; ethanol; tetrabutyl ammonium fluoride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; triethylamine; silver(l) oxide; zinc dibromide; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00062a035

upstream raw materials:

p-toluenesulfonyl chloride

<2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-(Hydroxymethyl)-3,3-dimethyl-2,4-dioxolan-5-yl>-3-azido-6-methoxy-3,4,5,6-tetrahydro-2H-pyran

2,3-O-isopropylidene-L-threitol

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

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