methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate

Base Information

• Chemical Name: methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate
• CAS No.: 1257841-36-3
• Molecular Formula: C₂₁H₂₉NO₈
• Molecular Weight: 423.463

Synonyms:methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate

Chemical Property of methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate

Chemical Property:

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Technology Process of methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate

There total 1 articles about methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate 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: 98.0%

BOC-O-benzyl-L-threonine N-hydroxysuccinimide ester (32886-43-4) + malonic acid dimethyl ester (108-59-8) → methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate (1257841-36-3)

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

BOC-O-benzyl-L-threonine N-hydroxysuccinimide ester; In tetrahydrofuran; mineral oil; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201000700

Reference yield: 89.0%

methyl (3S,4R)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxohexanoate (1257841-36-3) → (S)-N-tert-butoxycarbonyl-5-[(R)-1-(benzyloxy)ethyl]-3-methoxycarbonyltetramic acid (1257841-42-1)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 2h;

DOI:10.1002/ejoc.201000700

upstream raw materials:

BOC-O-benzyl-L-threonine N-hydroxysuccinimide ester

malonic acid dimethyl ester

Downstream raw materials:

(S)-N-tert-butoxycarbonyl-5-[(R)-1-(benzyloxy)ethyl]-3-methoxycarbonyltetramic acid

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