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

Base Information

• Chemical Name: Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester
• CAS No.: 131682-11-6
• Molecular Formula: C₂₃H₂₄N₂O₈
• Molecular Weight: 456.452

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

Chemical Property of Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester

There total 17 articles about Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-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:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester (131682-11-6)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / dimethylformamide / 1.5 h / 25 °C

2: 80percent aq. AcOH / 24 h / 25 °C

3: pyridine / CH₂Cl₂ / 1 h / 2 °C

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C

6: p-TsOH*H₂O / 3 h / 25 °C

7: NaBH₄ / aq. ethanol / 2 h / 25 °C

8: 82 percent / 80percent aq. AcOH / 15 h / 80 °C

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

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

11: Ac₂O / p-TsOH*H₂O / 1.5 h / 25 °C

12: 1.) 28percent aq. NH₄OH / 2.) p-TsOH*H₂O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h

With pyridine; lead(IV) acetate; potassium fluoride; ammonium hydroxide; sodium tetrahydroborate; oxalyl dichloride; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; toluene-4-sulfonic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.37.2555

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester (131682-11-6)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine / CH₂Cl₂ / 1 h / 2 °C

2: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

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

4: p-TsOH*H₂O / 3 h / 25 °C

5: NaBH₄ / aq. ethanol / 2 h / 25 °C

6: 82 percent / 80percent aq. AcOH / 15 h / 80 °C

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

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

9: Ac₂O / p-TsOH*H₂O / 1.5 h / 25 °C

10: 1.) 28percent aq. NH₄OH / 2.) p-TsOH*H₂O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h

With pyridine; lead(IV) acetate; potassium fluoride; ammonium hydroxide; sodium tetrahydroborate; oxalyl dichloride; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; toluene-4-sulfonic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.37.2555

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → Benzoic acid (1R,2S,3R,4S,5R)-3-acetylamino-4-benzyloxy-5-formyloxy-2-nitro-cyclopentylmethyl ester (131682-11-6)

Guidance literature:

Multi-step reaction with 13 steps

1: NaBH₄ / aq. ethanol / 1.5 h / 2 °C

2: NaH / dimethylformamide / 1.5 h / 25 °C

3: 80percent aq. AcOH / 24 h / 25 °C

4: pyridine / CH₂Cl₂ / 1 h / 2 °C

5: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

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

7: p-TsOH*H₂O / 3 h / 25 °C

8: NaBH₄ / aq. ethanol / 2 h / 25 °C

9: 82 percent / 80percent aq. AcOH / 15 h / 80 °C

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

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

12: Ac₂O / p-TsOH*H₂O / 1.5 h / 25 °C

13: 1.) 28percent aq. NH₄OH / 2.) p-TsOH*H₂O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h

With pyridine; lead(IV) acetate; potassium fluoride; ammonium hydroxide; sodium tetrahydroborate; oxalyl dichloride; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; toluene-4-sulfonic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.37.2555

upstream raw materials:

acetic anhydride

Benzoic acid (1R,4S,5R)-4-benzyloxy-5-formyloxy-2-nitro-cyclopent-2-enylmethyl ester

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Downstream raw materials:

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

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