(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

Base Information

• Chemical Name: (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
• CAS No.: 876175-60-9
• Molecular Formula: C₁₇H₂₄N₂O₄
• Molecular Weight: 320.389

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 71.0%

(3R,3aR,6R,6aS)-4-Allyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrole-2,3-diol (876175-59-6) + N-methylhydroxyamine hydrochloride (4229-44-1) → (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)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; for 20h; Heating;

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) → (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)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/ol052716a

Reference yield:

(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 (876175-58-5) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / H₂SO₄ / acetonitrile / 48 h / 25 °C

2: 71 percent / NaHCO₃ / H₂O; ethanol / 20 h / Heating

With sulfuric acid; sodium hydrogencarbonate; In ethanol; water; acetonitrile;

DOI:10.1021/ol052716a

upstream raw materials:

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

N-methylhydroxyamine hydrochloride

(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

(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

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