<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

Base Information

• Chemical Name: <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
• CAS No.: 147645-97-4
• Molecular Formula: C₂₈H₃₆O₆Si
• Molecular Weight: 496.676

Synonyms:<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

Chemical Property of <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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of <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

There total 6 articles about <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 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:

2,3-O-isopropylidene-L-threitol (50622-09-8) → <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)

Guidance literature:

Multi-step reaction with 5 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

With tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethyl sulfoxide; triethylamine; silver(l) oxide; zinc dibromide; In 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*),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)

Guidance literature:

Multi-step reaction with 4 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

With tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethyl sulfoxide; triethylamine; silver(l) oxide; zinc dibromide; In 2,2,4-trimethylpentane; dichloromethane;

DOI:10.1021/jo00062a035

Reference yield:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose (101331-92-4) → <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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 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

3: Ag₂O / 58 h / Ambient temperature

With tert.-butylhydroperoxide; n-butyllithium; bis(acetylacetonate)oxovanadium; silver(l) oxide; zinc dibromide; In 2,2,4-trimethylpentane; dichloromethane;

DOI:10.1021/jo00062a035

upstream raw materials:

methyl iodide

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:

1-deoxy-castanospermine

<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^*),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

<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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