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

Base Information

Chemical Name:(3aS,4R,6aR)-6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol
CAS No.:491578-00-8
Molecular Formula:C₁₆H₁₉IO₄
Molecular Weight:402.229
Hs Code.:

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

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

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

There total 9 articles about (3aS,4R,6aR)-6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[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: 93.0%

: 491577-99-2
(3aR,6aR)-6-benzyloxymethyl-5-iodo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 491578-00-8
(3aS,4R,6aR)-6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 1h;
DOI:10.1021/jm025557z

Reference yield:

: 117307-62-7,89291-75-8
(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

: 491578-00-8
(3aS,4R,6aR)-6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: I₂; pyridine / CCl₄

2: NaBH₄; CeCl₃*7H₂O

With pyridine; sodium tetrahydroborate; cerium(III) chloride; iodine; In tetrachloromethane;
DOI:10.1081/NCN-120021961

Reference yield:

: 1067238-45-2
(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

: 491578-00-8
(3aS,4R,6aR)-6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 80 °C / Inert atmosphere

2: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h / 20 °C / Molecular sieve

3: pyridine; iodine / 0 - 20 °C / Inert atmosphere

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

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride heptahydrate; iodine; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm3004009