(1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid

Base Information

Chemical Name:(1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid
CAS No.:136179-74-3
Molecular Formula:C₂₀H₂₅IO₅
Molecular Weight:472.32
Hs Code.:

Synonyms:

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Chemical Property of (1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid

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Technology Process of (1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid

There total 7 articles about (1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid 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:

: 4541-15-5
5-(benzyloxy)-1-pentanol

: 136179-74-3
(1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: PCC / CH₂Cl₂ / 1.5 h / Ambient temperature

2: toluene / 10 h / 100 °C / bath temp.

3: LiAlH₄ / diethyl ether / 0.17 h / ice bath

4: PCC / CH₂Cl₂

5: 1.) BuLi / 1.) THF, hexane, -5 deg C to r.t., 30 min; 2.) -15 deg C to r.t., 30 min

6: 82.6 percent / toluene / 17 h / 100 °C / bath temp.; hydroquinone for stabilization

7: 1.) aq. NaHCO₃; 2.) NaHCO₃, I₂, KI / 1.) H₂O, boiling, 30 min; 2.) r.t., 3.5 h

With lithium aluminium tetrahydride; n-butyllithium; iodine; sodium hydrogencarbonate; pyridinium chlorochromate; potassium iodide; In diethyl ether; dichloromethane; toluene;
DOI:10.1248/cpb.39.1359

Reference yield:

: 78999-24-3
5-benzyloxy-1-pentanal

: 136179-74-3
(1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: toluene / 10 h / 100 °C / bath temp.

2: LiAlH₄ / diethyl ether / 0.17 h / ice bath

3: PCC / CH₂Cl₂

4: 1.) BuLi / 1.) THF, hexane, -5 deg C to r.t., 30 min; 2.) -15 deg C to r.t., 30 min

5: 82.6 percent / toluene / 17 h / 100 °C / bath temp.; hydroquinone for stabilization

6: 1.) aq. NaHCO₃; 2.) NaHCO₃, I₂, KI / 1.) H₂O, boiling, 30 min; 2.) r.t., 3.5 h

With lithium aluminium tetrahydride; n-butyllithium; iodine; sodium hydrogencarbonate; pyridinium chlorochromate; potassium iodide; In diethyl ether; dichloromethane; toluene;
DOI:10.1248/cpb.39.1359

Reference yield:

: 136179-72-1
(3E)-8-Benzyloxy-3-methyl-1,3-octadiene

: 136179-74-3
(1R,2S,4S,5S,8S)-8-(4-Benzyloxy-butyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 82.6 percent / toluene / 17 h / 100 °C / bath temp.; hydroquinone for stabilization

2: 1.) aq. NaHCO₃; 2.) NaHCO₃, I₂, KI / 1.) H₂O, boiling, 30 min; 2.) r.t., 3.5 h

With iodine; sodium hydrogencarbonate; potassium iodide; In toluene;
DOI:10.1248/cpb.39.1359