<1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene

Base Information

• Chemical Name: <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene
• CAS No.: 160343-80-6
• Molecular Formula: C₂₃H₃₄O₆Si
• Molecular Weight: 434.605
• Mol file: 160343-80-6.mol

Synonyms:<1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene

Chemical Property of <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene

There total 6 articles about <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene 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%

benzyl chloroformate (501-53-1,94274-21-2) + (3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol (160343-79-3) → <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene (160343-80-6)

Guidance literature:

With dmap; In dichloromethane; 5 deg C, 1 h; 24 deg C, 30 min;

DOI:10.1016/S0040-4039(00)75990-9

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene (160343-80-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.) 1 M aq. HCl / 1.) pyridinium p-toluenesulfonate / 1.) 50 deg C, 1 h, 2.) THF, 24 - 25 deg C, 1 h

2: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 43 percent / DABCO / dimethylformamide / 1 h

5: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

6: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; dmap; sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; pyridinium p-toluenesulfonate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00095a021

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → <1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene (160343-80-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 43 percent / DABCO / dimethylformamide / 1 h

4: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

5: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00095a021

upstream raw materials:

benzyl chloroformate

(3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol

2,3-O-isopropylidene-D-ribonic-γ-lactone

(3aR,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-one

Downstream raw materials:

<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

<1R-(1α,2β,3β,4β,5β)>-5-Amino-4-(benzyloxy)-1,1':2,3-bis(isopropylidenedioxy)-1-methylcyclopentane

<1R-(1α,2β,3β,4β,5β)>-<4-(Benzyloxy)-1-(hydroxymethyl)-1,2,3-trihydroxycyclopent-5-yl>amino (2,3,4,6-O-tetrabenzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine