Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester
• CAS No.: 876175-69-8
• Molecular Formula: C₂₀H₂₆N₂O₆
• Molecular Weight: 390.436
• Mol file: 876175-69-8.mol

Synonyms:Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

There total 7 articles about Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl 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:

Acetic acid (2S,3S,4R)-2-((R)-1-acetoxy-2-oxo-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester (876175-68-7) → Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester (876175-69-8)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; In ethanol; at 25 ℃; for 5h;

DOI:10.1021/ol052716a

Reference yield:

(3aR,4aS,5R,7aS,7bR)-7-Allyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrol-5-ol (876175-57-4) → Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester (876175-69-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / NaH / tetrahydrofuran / 0.1 h / Heating

2: 97 percent / H₂SO₄ / acetonitrile / 48 h / 25 °C

3: hydrochloric acid / 18 h / 0 °C

4: 910 mg / pyridine; DMAP / 12 h / 25 °C

5: HgO; HgCl₂ / H₂O; acetone / 1.5 h / Heating

6: 95 mg / pyridine; NH₂OH*HCl / ethanol / 5 h / 25 °C

With pyridine; hydrogenchloride; dmap; sulfuric acid; hydroxylamine hydrochloride; sodium hydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; ethanol; water; acetone; acetonitrile;

DOI:10.1021/ol052716a

Reference yield:

(3R,3aR,6R,6aS)-4-Allyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrole-2,3-diol (876175-59-6) → Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester (876175-69-8)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrochloric acid / 18 h / 0 °C

2: 910 mg / pyridine; DMAP / 12 h / 25 °C

3: HgO; HgCl₂ / H₂O; acetone / 1.5 h / Heating

4: 95 mg / pyridine; NH₂OH*HCl / ethanol / 5 h / 25 °C

With pyridine; hydrogenchloride; dmap; hydroxylamine hydrochloride; mercury dichloride; mercury(II) oxide; In ethanol; water; acetone;

DOI:10.1021/ol052716a

upstream raw materials:

Acetic acid (2S,3S,4R)-2-((R)-1-acetoxy-2-oxo-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

(3aR,4aS,5R,7aS,7bR)-7-Allyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrol-5-ol

(3R,3aR,6R,6aS)-4-Allyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrole-2,3-diol

(3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole

Downstream raw materials:

Acetic acid (1S,5R,6S,7R,8R,9R)-6-acetoxy-5-benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester

acetic acid 7-acetoxy-6-benzyloxy-3a,4,6,7,7a,8-hexahydro-3H,5H-2-oxa-1,4a-diaza-s-indacen-8-yl ester