(1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one

Base Information

• Chemical Name: (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one
• CAS No.: 190791-71-0
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422

Synonyms:(1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one

Chemical Property of (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one

Chemical Property:

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Technology Process of (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one

There total 4 articles about (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one 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: 88.0%

phosgene (75-44-5) + 1,6-Anhydro-2-O-benzyl-4-(cyclohexylamino)-4-desoxy-β-D-glucopyranose (97119-82-9) → (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.02,6]undecan-4-one (190791-71-0)

Guidance literature:

With pyridine; In dichloromethane; toluene; -70 -> -10 deg C;

DOI:10.1071/C96154

Reference yield: 63.0%

chloroformic acid ethyl ester (541-41-3) + 1,6-Anhydro-2-O-benzyl-4-(cyclohexylamino)-4-desoxy-β-D-glucopyranose (97119-82-9) → (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.02,6]undecan-4-one (190791-71-0)

Guidance literature:

With triethylamine; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1071/C96154

Reference yield:

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose (33208-46-7) → (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.02,6]undecan-4-one (190791-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / butan-1-ol / 14 h / 110 °C

2: 88 percent / pyridine / CH₂Cl₂; toluene / -70 -> -10 deg C

With pyridine; In dichloromethane; toluene; butan-1-ol;

DOI:10.1071/C96154

upstream raw materials:

phosgene

1,6-Anhydro-2-O-benzyl-4-(cyclohexylamino)-4-desoxy-β-D-glucopyranose

chloroformic acid ethyl ester

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose

Downstream raw materials:

Acetic acid (1S,2R,6S,7R,8R)-3-cyclohexyl-4-oxo-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester

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