(3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

Base Information

• Chemical Name: (3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS No.: 805245-39-0
• Molecular Formula: C₂₈H₂₇IO₄
• Molecular Weight: 554.424
• Mol file: 805245-39-0.mol

Synonyms:(3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-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: 97.0%

(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (805245-38-9) → (3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-39-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2004.08.047 DOI:10.1081/NCN-200060286

Reference yield:

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (88559-56-2) → (3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / I₂; pyridine / CCl₄ / 12 h / 20 °C

2: 97 percent / NaBH₄; CeCl₃ / methanol / 0.5 h / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; iodine; In methanol; tetrachloromethane;

DOI:10.1016/j.bmcl.2004.08.047 DOI:10.1081/NCN-200060286

Reference yield:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) → (3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-39-0)

Guidance literature:

Multi-step reaction with 7 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

7.1: sodium tetrahydroborate; cerium(III) chloride / methanol; water / 1 h / 0 °C

With pyridine; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 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; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Wittig Reaction / 2.1: Swern Oxidation / 3.1: Grignard Reaction;

upstream raw materials:

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

(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

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

(3aS,4R,6aR)-6-(benzyloxymethyl)-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol