methyl (Z)-(1R^*,5S^*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate

Base Information

• Chemical Name: methyl (Z)-(1R^*,5S^*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate
• CAS No.: 122834-24-6
• Molecular Formula: C₂₇H₃₇N₃O₇
• Molecular Weight: 515.607

Synonyms:

Chemical Property of methyl (Z)-(1R^*,5S^*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate

Chemical Property:

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Useful:

Technology Process of methyl (Z)-(1R^*,5S^*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate

There total 7 articles about methyl (Z)-(1R^*,5S^*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate 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: 73.0%

methyl (E)-(3'R*,4'S*)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-butenoate (122834-23-5,122920-87-0) → methyl (E)-(1'R*,5'S*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate (122834-24-6,122920-88-1)

Guidance literature:

With phosphate buffer; chlorine;

DOI:10.1016/0040-4020(89)80100-0

Reference yield: 49.0%

methyl (Z)-(3'R*,4'S*)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-butenoate (122834-23-5,122920-87-0) → methyl (Z)-(1R*,5S*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate (122834-24-6,122920-88-1)

Guidance literature:

With phosphate buffer; chlorine;

DOI:10.1016/0040-4020(89)80100-0

Reference yield:

benzoyl chloride (98-88-4) → methyl (E)-(1'R*,5'S*)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-2-butenoate (122834-24-6,122920-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) triethyl amine, hydrogen sulfide, 2) triethyl amine / 1) dichloromethane, 0 deg C, 1 h, 2) dichloromethane, -22 deg C, overnight

2: 73 percent / Cl₂, phosphate buffer

With phosphate buffer; hydrogen sulfide; chlorine; triethylamine;

DOI:10.1016/0040-4020(89)80100-0

upstream raw materials:

methyl (E)-(3'R^*,4'S^*)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-butenoate

benzoyl chloride

methyl (Z)-(3'R^*,4'S^*)-2-(3-benzoylamino-4-methylthio-2-oxo-azetidin-1-yl)-3-tert.-butoxymethyl-4-(N,N-diisopropylcarbamoyloxy)-2-butenoate

Downstream raw materials:

methyl (1R^*,8R^*)-8-benzoylamino-4-(N,N-diisopropylcarbamoyloxymethyl)-7-oxo-2-oxa-6-azabicyclo<4.2.0>oct-4-en-5-carboxylate

(1R^*,5S^*)-6-<4-(N,N-diisopropylcarbamoyloxymethyl)-2-oxo-2,5-dihydrofuran-3-yl>-3-phenyl-4-oxa-2,6-diazabicyclo<3.2.0>hept-3-en-7-one

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