1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

Base Information

Chemical Name:1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid
CAS No.:931095-17-9
Molecular Formula:C₃₅H₄₀O₇
Molecular Weight:572.698
Hs Code.:

Synonyms:1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

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Chemical Property of 1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

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Technology Process of 1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

There total 6 articles about 1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic 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: 69.0%

: 931095-16-8
benzyloxyacetic acid (1R,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyl ester

: 931095-17-9
1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

Guidance literature:: With chloro-trimethyl-silane; lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 - 65 ℃;
DOI:10.1021/ol0630189

Reference yield:

: 931095-27-1
(1S,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enol

: 931095-17-9
1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / PPh₃; DEAD / tetrahydrofuran; CH₂Cl₂ / 24 h / 0 - 4 °C

2: 69 percent / TMSCl; LiHMDS / tetrahydrofuran; toluene / -78 - 65 °C

With chloro-trimethyl-silane; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; 2: Claisen-Ireland rearrangement;
DOI:10.1021/ol0630189

Reference yield:

: 931095-26-0
(1R)-1-[(1S,4S,5R,6R)-6-benzyloxy-5-methoxymethyl-4-triethylsilanyloxy-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-acetaldehyde

: 931095-17-9
1-benzyloxy-1-{(1S,4R,5S,6S)-5-benzyloxy-6-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-4-methoxymethyl-cyclohex-2-enyl}-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: tBuOK / tetrahydrofuran / 0.08 h / Heating

1.2: 91 percent / tetrahydrofuran / 0.17 h / 20 °C

2.1: 100 percent / NH₄F / methanol / 3 h / 20 °C

3.1: 76 percent / PPh₃; DEAD / tetrahydrofuran; CH₂Cl₂ / 24 h / 0 - 4 °C

4.1: 69 percent / TMSCl; LiHMDS / tetrahydrofuran; toluene / -78 - 65 °C

With ammonium fluoride; chloro-trimethyl-silane; potassium tert-butylate; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.2: Wittig olefination / 4.1: Claisen-Ireland rearrangement;
DOI:10.1021/ol0630189