<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

Base Information

• Chemical Name: <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
• CAS No.: 147645-98-5
• Molecular Formula: C₂₈H₄₀O₆Si
• Molecular Weight: 500.707

Synonyms:<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

Chemical Property of <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

Chemical Property:

Purity/Quality:

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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>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-ol

There total 7 articles about <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 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: 92.0%

<2S-<2α(2R*,4R*),6α>>-2-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-2,4-dioxolan-5-yl>-6-methoxy-2H-pyran-3(6H)-one (147645-97-4) → <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)

Guidance literature:

With ethanol; potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -100 ℃; for 2h;

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>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-ol (147645-98-5)

Guidance literature:

Multi-step reaction with 6 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

With tert.-butylhydroperoxide; 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>-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-ol (147645-98-5)

Guidance literature:

Multi-step reaction with 5 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

With tert.-butylhydroperoxide; 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:

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

2,3-O-isopropylidene-L-threitol

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

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

Downstream raw materials:

<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

<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

1-deoxy-castanospermine

<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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