O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Base Information

• Chemical Name: O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol
• CAS No.: 640279-67-0
• Molecular Formula: C₂₅H₃₁NO₅
• Molecular Weight: 425.525

Synonyms:O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Chemical Property of O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

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Technology Process of O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

There total 2 articles about O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol 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:

1-nitro-1-phenylmethane (622-42-4) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (640279-67-0) + O-[2-hydroxy-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With aluminum oxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2004.04.005

Reference yield:

1-nitro-1-phenylmethane (622-42-4) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (640279-67-0) + O-[(2S)-hydroxy-(3S)-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With activated A₂O₃; at 20 ℃; for 1h;

DOI:10.1021/jo0358269

Reference yield:

O-[(2S)-hydroxy-(3R)-3-nitro-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (640279-67-0) → (2S,3R)-3-Amino-2-hydroxy-3-phenyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Guidance literature:

With hydrogen; nickel; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2003.09.154

upstream raw materials:

1-nitro-1-phenylmethane

(1R,3R,4S)-8-phenylmenthyl glyoxylate

Downstream raw materials:

(+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate

methyl (2S)-acetoxy-(3R)-tert-butoxycarbonylamino-3-phenylpropionate

(2S,3R)-2-Acetoxy-3-tert-butoxycarbonylamino-3-phenyl-propionic acid

O-[(3R)-tert-butoxycarbonylamino-(2S)-hydroxy-3-phenylpropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

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