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

Base Information

• Chemical Name: <1S-(1α,4α,5α)>-3-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene
• CAS No.: 160343-87-3
• Molecular Formula: C₂₃H₃₆O₅Si
• Molecular Weight: 420.621
• Mol file: 160343-87-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about <1S-(1α,4α,5α)>-3-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-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: 69.0%

p-methoxybenzyl chloride (824-94-2) + (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)>-3-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene (160343-87-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 24 ℃; for 3h;

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

Reference yield: 16.0%

p-methoxybenzyl chloride (824-94-2) + (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)>-3-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene (160343-87-3) + <1S-(1α,4α,5α)>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-3-<(4-methoxybenzyl)oxy>methyl-2-cyclopentene

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; paraffin; for 3h; Ambient temperature;

DOI:10.1021/jo00095a021

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → <1S-(1α,4α,5α)>-3-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene (160343-87-3)

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: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

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

DOI:10.1021/jo00095a021

upstream raw materials:

p-methoxybenzyl chloride

(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:

<1S-(1α,4α,5α)>-3-(Hydroxymethyl)-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

<1R-(1α,2β,3β,4β,5β)>-5-Amino-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-1,4-cyclopentanediol

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