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

Base Information

Chemical Name:benzyloxyacetic acid (1R,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyl ester
CAS No.:931095-16-8
Molecular Formula:C₃₅H₄₀O₇
Molecular Weight:572.698
Hs Code.:

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

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

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

There total 10 articles about benzyloxyacetic acid (1R,4S,5S,6R)-5-benzyloxy-4-[(1R)-1-(4-methoxy-benzyloxy)-allyl]-6-methoxymethyl-cyclohex-2-enyl 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: 76.0%

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

: 30379-55-6
benzyloxyacetic acid

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

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; at 0 - 4 ℃; for 24h;
DOI:10.1021/ol0630189

Reference yield: 76.0%

: 30379-55-6
benzyloxyacetic acid

: (1S)-{5(R)-benzyloxy-4(S)-[1(R)-(4-methoxybenzyloxy)allyl]-6(R)-methoxymethyl}cyclohex-2-enol

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

Guidance literature:: (1S)-{5(R)-benzyloxy-4(S)-[1(R)-(4-methoxybenzyloxy)allyl]-6(R)-methoxymethyl}cyclohex-2-enol; With triphenylphosphine; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

benzyloxyacetic acid; In tetrahydrofuran; dichloromethane; for 0.0833333h; Inert atmosphere;

With diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; at 0 - 4 ℃; for 24.5h; Inert atmosphere;
DOI:10.1002/chem.201200257

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

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

Guidance literature:: Multi-step reaction with 3 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

With ammonium fluoride; potassium tert-butylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1.2: Wittig olefination;
DOI:10.1021/ol0630189