(1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane

Base Information

• Chemical Name: (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane
• CAS No.: 113299-34-6
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 426.628
• Mol file: 113299-34-6.mol

Synonyms:

Chemical Property of (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane

There total 7 articles about (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane 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:

(3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (112543-75-6) → (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane (112543-73-4,112574-57-9,112574-58-0,113299-34-6)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / Ambient temperature

2: PCC, molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

3: 80 percent / sodium borohydride / methanol / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; molecular sieve; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00242a016

Reference yield:

(1S,2S,3S,4S)-2-acetoxy-1-(acetoxymethyl)-3,4-(isopropylidenedioxy)cyclopentane (105285-29-8) → (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane (112543-73-4,112574-57-9,112574-58-0,113299-34-6)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium methoxide / methanol / 0 °C

2: imidazole / dimethylformamide / Ambient temperature

3: PCC, molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

4: 80 percent / sodium borohydride / methanol / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; molecular sieve; sodium methylate; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00242a016

Reference yield:

(1S,2S,3S,4S)-1-<((tert-butyldiphenylsilyl)-oxy)methyl>-2,3-(isopropylidenedioxy)cyclopenetane (112543-73-4) → (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane (112543-73-4,112574-57-9,112574-58-0,113299-34-6)

Guidance literature:

Multi-step reaction with 3 steps

1: PCC, molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

2: 80 percent / sodium borohydride / methanol / 1 h / 0 °C

With sodium tetrahydroborate; molecular sieve; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1021/jo00242a016

upstream raw materials:

(3aS,6aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

(1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane

(1S,2S,4S)-4-(t-butyldiphenylsilyloxymethyl)-1,2-isopropylidenedioxy-3-cyclopentanone

(3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Downstream raw materials:

(1S,2S,3R,4R)-(+)-4-(Hydroxymethyl)cyclopentane-1,2,3-triol

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

(1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentane

(1R,2R,3S,4R)-4-azido-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2,3-(isopropylidenedioxy)cyclopentane