Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester
CAS No.:131603-35-5
Molecular Formula:C₂₃H₂₅NO₆
Molecular Weight:411.455
Hs Code.:

Synonyms:Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl 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 (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester

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Technology Process of Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester

There total 18 articles about Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl 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: 63.0%

: 131603-34-4
Benzoic acid (1R,2R,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester

: 131603-35-5
Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 3h;
DOI:10.1016/S0040-4020(01)89060-8 DOI:10.1248/cpb.37.2555

Reference yield: 62.0%

: 131682-11-6
Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester

: 131603-35-5
Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 3h;
DOI:10.1016/S0040-4020(01)89060-8 DOI:10.1248/cpb.37.2555

Reference yield:

: 121403-51-8,131603-31-1
Benzoic acid 2-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-oxo-ethyl ester

: 131603-35-5
Benzoic acid (1R,2R,3S,4R)-4-acetylamino-3-benzyloxy-2-formyloxy-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C

2: p-TsOH*H₂O / 3 h / 25 °C

3: NaBH₄ / aq. ethanol / 2 h / 25 °C

4: 82 percent / 80percent aq. AcOH / 15 h / 80 °C

5: Pb(OAc)4 / benzene / 0.67 h / 25 °C

6: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C

7: Ac₂O / p-TsOH*H₂O / 1.5 h / 25 °C

8: 1.) 28percent aq. NH₄OH / 2.) p-TsOH*H₂O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h

9: 63 percent / n-Bu₃SnH, AIBN / benzene / 3 h / 80 °C

With lead(IV) acetate; potassium fluoride; ammonium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic anhydride; acetic acid; 18-crown-6 ether; toluene-4-sulfonic acid; In ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.37.2555