(1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ⁴-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ⁴-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester
• CAS No.: 91026-09-4
• Molecular Formula: C₁₇H₂₃NO₆S
• Molecular Weight: 369.439

Synonyms:(1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ⁴-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester

Chemical Property of (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ⁴-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester

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Technology Process of (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ⁴-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester

There total 8 articles about (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ⁴-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester 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: 51.0%

(1S,3R)-3-(2-Methoxymethoxy-ethyl)-5-methyl-1-oxo-3,6-dihydro-1H-1λ4-[1,2]thiazine-2-carboxylic acid benzyl ester (91026-05-0,91026-06-1) → (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ4-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester (91026-09-4) + 3-(2-Methoxymethoxy-ethyl)-5-methyl-1,1-dioxo-3,6-dihydro-1H-1λ6-[1,2]thiazine-2-carboxylic acid benzyl ester (91026-08-3) + (1R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3,3-dioxo-7-oxa-3λ6-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester (91034-49-0,107381-37-3)

Guidance literature:

With dipotassium hydrogenphosphate; trifluoroacetyl peroxide; In dichloromethane; at -10 ℃;

DOI:10.1021/jo00383a001

Reference yield:

methyl 5-methyl-2,4-hexadienoate (52148-91-1) → (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ4-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester (91026-09-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA, HMPA, 2.) acetic acid / 1.) THF, -78 deg C

2: LiAlH₄ / tetrahydrofuran

3: diisopropylethylamine / CH₂Cl₂

4: toluene / 3 h / Ambient temperature

5: o-dichlorobenzene / 180 °C

6: 18 percent / pertrifluoroacetic acid, K₂HPO₄ / CH₂Cl₂

With N,N,N,N,N,N-hexamethylphosphoric triamide; dipotassium hydrogenphosphate; lithium aluminium tetrahydride; acetic acid; N-ethyl-N,N-diisopropylamine; 1,2-dichloro-benzene; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

(E)-methyl 5-methylhexa-3,5-dienoate (91026-03-8) → (1R,3R,5S,6R)-5-(2-Methoxymethoxy-ethyl)-1-methyl-3-oxo-7-oxa-3λ4-thia-4-aza-bicyclo[4.1.0]heptane-4-carboxylic acid benzyl ester (91026-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran

2: diisopropylethylamine / CH₂Cl₂

3: toluene / 3 h / Ambient temperature

4: o-dichlorobenzene / 180 °C

5: 18 percent / pertrifluoroacetic acid, K₂HPO₄ / CH₂Cl₂

With dipotassium hydrogenphosphate; lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; 1,2-dichloro-benzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

(1S,3R)-3-(2-Methoxymethoxy-ethyl)-5-methyl-1-oxo-3,6-dihydro-1H-1λ⁴-[1,2]thiazine-2-carboxylic acid benzyl ester

methyl 5-methyl-2,4-hexadienoate

3,3-dimethyl acrylaldehyde

O-benzyl carbamate

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