(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Base Information

• Chemical Name: (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one
• CAS No.: 805245-38-9
• Molecular Formula: C₂₈H₂₅IO₄
• Molecular Weight: 552.409
• Mol file: 805245-38-9.mol

Synonyms:(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Chemical Property of (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

There total 14 articles about (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one 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: 72.0%

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (88559-56-2) → (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (805245-38-9)

Guidance literature:

With pyridine; iodine; In dichloromethane; at 0 - 20 ℃; for 6h;

Reference yield:

(1R,4S,5S)-2-iodo-4,5-isopropylidenedioxy-1-(trityloxymethyl)cyclopent-2-enol → (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (805245-38-9)

Guidance literature:

With aluminum oxide; dipyridinium dichromate; In dichloromethane; at 20 ℃; for 12h; Temperature; Reagent/catalyst; Molecular sieve; Large scale;

Reference yield:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) → (3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (805245-38-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 7 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

2.2: 1 h / -78 - 20 °C

3.1: tetrahydrofuran / 1 h / -78 °C

4.1: tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride / dichloromethane / 48 h / 20 °C

5.1: dipyridinium dichromate / molecular sieve / N,N-dimethyl-formamide / 48 h / 20 °C

6.1: pyridine; iodine / dichloromethane / 6 h / 0 - 20 °C

With pyridine; dipyridinium dichromate; oxalyl dichloride; potassium tert-butylate; iodine; dimethyl sulfoxide; tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride; molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig Reaction / 2.1: Swern Oxidation / 3.1: Grignard Reaction;

upstream raw materials:

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

2,2-dimethoxy-propane

2,3-O-isopropylidene-D-ribofuranose

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

Downstream raw materials:

RX-3117

C₂₉H₄₁FN₂O₇SSi₂

(3R,4S,6aR)-3-benzoyl-1-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione