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

Base Information

• Chemical Name: 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
• CAS No.: 876175-61-0
• Molecular Formula: C₂₁H₂₈N₂O₆
• Molecular Weight: 404.463

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 9 articles about 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 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: 80.0%

(1S,5R,6S,7R,8R,9R)-5-Benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.03,7]dodecane-6,8-diol (876175-60-9) + acetic anhydride (108-24-7) → Acetic acid (1S,5R,6S,7R,8R,9R)-6-acetoxy-5-benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.03,7]dodec-8-yl ester (876175-61-0)

Guidance literature:

With pyridine; dmap; at 25 ℃; for 12h;

DOI:10.1021/ol052716a

Reference yield: 27.0%

Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester (876175-69-8) + N-methylhydroxyamine hydrochloride (4229-44-1) → Acetic acid (1S,5R,6S,7R,8R,9R)-6-acetoxy-5-benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.03,7]dodec-8-yl ester (876175-61-0)

Guidance literature:

With pyridine; at 25 ℃; for 20h;

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 (1S,5R,6S,7R,8R,9R)-6-acetoxy-5-benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.03,7]dodec-8-yl ester (876175-61-0)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 71 percent / NaHCO₃ / H₂O; ethanol / 20 h / Heating

4: 80 percent / pyridine; DMAP / 12 h / 25 °C

With pyridine; dmap; sulfuric acid; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1021/ol052716a

upstream raw materials:

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

N-methylhydroxyamine hydrochloride

(1S,5R,6S,7R,8R,9R)-5-Benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.0^3,7]dodecane-6,8-diol

acetic anhydride

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