(1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol

Base Information

• Chemical Name: (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol
• CAS No.: 681853-92-9
• Molecular Formula: C₂₅H₃₂O₄Si
• Molecular Weight: 424.612
• Mol file: 681853-92-9.mol

Synonyms:(1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol

Chemical Property of (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol

There total 11 articles about (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-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: 95.0%

(1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol (952418-10-9) → (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol (681853-92-9)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/jo0356762

Reference yield: 95.0%

C27H36SiO4 (902799-70-6) → (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol (681853-92-9)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 20 ℃;

DOI:10.1081/NCN-200061832

Reference yield:

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → (1R,4S,5S)-(+)-4,5-isopropylidenedioxy-1-(tert-butyldiphenylsilyloxymethyl)-2-cyclopenten-1-ol (681853-92-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

1.2: 86 percent / tetrahydrofuran / 7 h / 0 - 20 °C

2.1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3.1: 96 percent / tetrahydrofuran / 1 h / -78 °C

4.1: 95 percent / Neolyst dichloride^TM / CH₂Cl₂ / 48 h / 20 °C

With oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; Neolyst dichloride^TM; In tetrahydrofuran; dichloromethane; 1.2: Wittig reaction / 2.1: Swern oxidation / 3.1: Grignard reaction;

DOI:10.1016/j.tet.2007.06.100

upstream raw materials:

(1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol

C₂₇H₃₆SiO₄

2,3-O-isopropylidene-D-ribofuranose

D-ribose

Downstream raw materials:

neplanocin A

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

(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol

(3aR,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one