Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

Base Information

Chemical Name:Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester
CAS No.:119826-16-3
Molecular Formula:C₂₁H₂₁NO₈
Molecular Weight:415.4
Hs Code.:

Synonyms:Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

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Chemical Property of Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

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Technology Process of Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

There total 14 articles about Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl 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:

: 57099-04-4
3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

: 119826-16-3
Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

Guidance literature:: Multi-step reaction with 7 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

With pyridine; lead(IV) acetate; potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; 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:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 119826-16-3
Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

Guidance literature:: Multi-step reaction with 10 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

With pyridine; lead(IV) acetate; potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; 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:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 119826-16-3
Benzoic acid (3R,4R)-4-benzyloxy-3-formyloxy-2-nitromethyl-5-oxo-pentyl ester

Guidance literature:: Multi-step reaction with 9 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

With pyridine; lead(IV) acetate; potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; 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