(3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Base Information

• Chemical Name: (3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole
• CAS No.: 341553-93-3
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Mol file: 341553-93-3.mol

Synonyms:(3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Chemical Property of (3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

There total 1 articles about (3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole 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: 88.0%

benzyl bromide (100-39-0) + (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol (192118-38-0) → (3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (341553-93-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol015783n

Reference yield: 97.0%

(3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (341553-93-3) → (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane (341553-94-4)

Guidance literature:

With trifluoroacetic acid; In water; at 60 ℃;

DOI:10.1021/ol015783n

Reference yield:

(3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (341553-93-3) → Diphenyl-carbamic acid 2-acetylamino-9-((1S,3R,4S)-3-hydroxy-4-hydroxymethyl-cyclopentyl)-9H-purin-6-yl ester

Guidance literature:

Multi-step reaction with 10 steps

1.1: 97 percent / TFA / H₂O / 60 °C

2.1: 79 percent / pyridine / 0 °C

3.1: NaH; CS₂; MeI / tetrahydrofuran / 0 - 20 °C

3.2: 76 percent / Bu₃SnH; AIBN / toluene / Heating

4.1: 82 percent / H₂ / Pd(OH)2 / methanol

5.1: 85 percent / PPTS / CH₂Cl₂ / 20 °C

6.1: 84 percent / TBAF / tetrahydrofuran / 20 °C

7.1: 99 percent / imidazole / tetrahydrofuran / 0 - 20 °C

8.1: 98 percent / pyridine / 0 °C

9.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; carbon disulfide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; trifluoroacetic acid; methyl iodide; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;

DOI:10.1021/ol015783n

upstream raw materials:

benzyl bromide

(1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol

Downstream raw materials:

(-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane

(+)-(3R,5R)-1-fluoro-3-hydroxymethyl-5-O-benzyloxycyclopent-1-ene

(+)-(1R,2S,4R)-1-O-benzyloxy-2-hydroxyl-4-hydroxymethylcyclopentane

(+)-(3R,5R)-1-fluoro-3-(O-tert-butyldimethylsilyloxymethyl)-5-O-benzyloxycyclopent-1-ene