(+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone

Base Information

• Chemical Name: (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone
• CAS No.: 87325-87-9
• Molecular Formula: C₁₇H₂₃NO₇
• Molecular Weight: 353.372

Synonyms:(+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone

Chemical Property of (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone

There total 4 articles about (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone 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: 36.0%

(+/-)-<1α,4α,5α>-methyl-7-(2,4-dimethoxybenzyl)-2,6-dioxo-4-methyl-3-oxa-7-azabicyclo<3.2.0>heptane-1-carboxylate (85508-71-0) → (+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone (87325-87-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)91966-0

Reference yield:

(+/-)-(R*,S*)-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4,4-bis(carboxylic acid) (85486-81-3) → (+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone (87325-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1: conc HCl / tetrahydrofuran / 16 h / 25 °C

2: diethyl ether

3: 36 percent / sodium borohydride / methanol / 1 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4020(01)91966-0

Reference yield:

(+/-)-<1α,4α,5α>-7-(2,4-dimethoxybenzyl)-2,6-dioxo-4-methyl-3-oxa-7-azabicyclo<3.2.0>heptane-1-carboxylic acid (85486-82-4,85761-35-9) → (+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-methoxycarbonyl-4-hydroxymethyl-2-azetidinone (87325-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: 36 percent / sodium borohydride / methanol / 1 h / 0 °C

With sodium tetrahydroborate; In methanol; diethyl ether;

DOI:10.1016/S0040-4020(01)91966-0

upstream raw materials:

(+/-)-<1α,4α,5α>-methyl-7-(2,4-dimethoxybenzyl)-2,6-dioxo-4-methyl-3-oxa-7-azabicyclo<3.2.0>heptane-1-carboxylate

(+/-)-(R^*,S^*)-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4,4-bis(carboxylic acid)

(+/-)-<1α,4α,5α>-7-(2,4-dimethoxybenzyl)-2,6-dioxo-4-methyl-3-oxa-7-azabicyclo<3.2.0>heptane-1-carboxylic acid

(+/-)-<3S-<3α(S^*),4α>>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-ethoxycarbonyl-2-azetidinone-4-carboxylic acid

Downstream raw materials:

(+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-methoxycarbonyl-4-acetoxymethyl-2-azetidinone

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