Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

Base Information

Chemical Name:Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester
CAS No.:389620-81-9
Molecular Formula:C₁₇H₁₇IO₅
Molecular Weight:428.223
Hs Code.:

Synonyms:Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

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Technology Process of Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

There total 7 articles about Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester 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: 27.0%

: 389620-80-8
(4aS,5S,6R,7aS,7bS)-5-benzoyloxy-5,6,7a,7b-tetrahydro-6-iodomethyl-2H-1,7-dioxacyclopent[cd]inden-4(4aH)-one

: 389620-81-9
Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1016/S0008-6215(01)00211-7

Reference yield: 27.0%

: 389620-80-8
(4aS,5S,6R,7aS,7bS)-5-benzoyloxy-5,6,7a,7b-tetrahydro-6-iodomethyl-2H-1,7-dioxacyclopent[cd]inden-4(4aH)-one

: 389620-81-9
Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

Guidance literature:: With 4-methylmorpholine N-oxide; In tetrahydrofuran; at 0 - 20 ℃; for 3h;
DOI:10.1016/S0008-6215(01)00211-7

Reference yield:

: 98-88-4
benzoyl chloride

: 389620-81-9
Benzoic acid (4S,4aR,5S,6S,7aS,7bS)-4-hydroxy-6-iodomethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-5-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / pyridine / 20 °C

2: 94 percent / NaI / dimethylformamide / 6 h / 80 °C

3: 55 percent / NMO*H₂O / 3 h / 0 - 20 °C

4: 27 percent / DIBAL / tetrahydrofuran / 3 h / -78 °C

With pyridine; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; 3: Pauson-Khand;
DOI:10.1016/S0008-6215(01)00211-7