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

Base Information

• Chemical Name: <2S-<2α(2R^*,4R^*),3β,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-<(methylsulfonyl)oxy>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran
• CAS No.: 147646-07-9
• Molecular Formula: C₂₉H₄₂O₈SSi
• Molecular Weight: 578.799

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

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

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

There total 8 articles about <2S-<2α(2R^*,4R^*),3β,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-<(methylsulfonyl)oxy>-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: 84.0%

methanesulfonyl chloride (124-63-0) + <2S-<2α(2R*,4R*),3β,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-ol (147645-98-5) → <2S-<2α(2R*,4R*),3β,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-<(methylsulfonyl)oxy>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-07-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; 1.) 0 deg C, 10 min, 2.) r.t., 3.5 h;

DOI:10.1021/jo00062a035

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → <2S-<2α(2R*,4R*),3β,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-<(methylsulfonyl)oxy>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-07-9)

Guidance literature:

Multi-step reaction with 7 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

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

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*),3β,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-3-<(methylsulfonyl)oxy>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran (147646-07-9)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jo00062a035

upstream raw materials:

methanesulfonyl chloride

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

2,3-O-isopropylidene-L-threitol

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

Downstream raw materials:

<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

<2S-<2α(2R^*,4R^*),3α,6α>>-2-<1-<<(tert-Butyldiphenylsilyl)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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