Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine

Base Information

• Chemical Name: Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine
• CAS No.: 211567-33-8
• Molecular Formula: C₂₃H₃₃Cl₂N₂O₆P
• Molecular Weight: 535.405

Synonyms:Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine

Chemical Property of Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine

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Technology Process of Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine

There total 8 articles about Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine 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: 87.0%

N,N-di(2-chloroethyl)amidophosphoric acid dichloride (127-88-8) + cyclohexyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (211567-30-5) → Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ5-phospha-cyclopenta[a]naphthalen-2-yl)-amine (211567-33-8)

Guidance literature:

In dichloromethane; 0 deg C, then room temp., overnight;

DOI:10.1016/S0008-6215(98)00056-1

Reference yield:

cyclohexyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (21559-72-8) → Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ5-phospha-cyclopenta[a]naphthalen-2-yl)-amine (211567-33-8)

Guidance literature:

Multi-step reaction with 5 steps

1: ZnCl₂

2: 76 percent / pyridine / 24 h / 0 °C

3: 72 percent / anh. NaOAc / 2-methoxy-ethanol; H₂O / 12 h / Heating

4: 94 percent / KOH / aq. ethanol / 6 h / Heating

5: 87 percent / CH₂Cl₂ / 0 deg C, then room temp., overnight

With pyridine; potassium hydroxide; sodium acetate; zinc(II) chloride; In ethanol; dichloromethane; 2-methoxy-ethanol; water;

DOI:10.1016/S0008-6215(98)00056-1

Reference yield:

cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (21588-60-3) → Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-cyclohexyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ5-phospha-cyclopenta[a]naphthalen-2-yl)-amine (211567-33-8)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOMe / methanol / 30 h / Ambient temperature

2: ZnCl₂

3: 76 percent / pyridine / 24 h / 0 °C

4: 72 percent / anh. NaOAc / 2-methoxy-ethanol; H₂O / 12 h / Heating

5: 94 percent / KOH / aq. ethanol / 6 h / Heating

6: 87 percent / CH₂Cl₂ / 0 deg C, then room temp., overnight

With pyridine; potassium hydroxide; sodium methylate; sodium acetate; zinc(II) chloride; In methanol; ethanol; dichloromethane; 2-methoxy-ethanol; water;

DOI:10.1016/S0008-6215(98)00056-1

upstream raw materials:

N,N-di(2-chloroethyl)amidophosphoric acid dichloride

cyclohexyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

cyclohexyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside

cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside

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