((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ⁶-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ⁶-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester
• CAS No.: 107302-10-3
• Molecular Formula: C₁₅H₁₉NO₅S
• Molecular Weight: 325.386

Synonyms:((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ⁶-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester

Chemical Property of ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ⁶-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester

Chemical Property:

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Technology Process of ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ⁶-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester

There total 7 articles about ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ⁶-[1,2]oxathiocin-6-yl)-carbamic 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: 70.0%

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) → ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ6-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester (107302-10-3)

Guidance literature:

With hydrogenchloride; In methanol; at 50 ℃; for 4h;

DOI:10.1021/jo00383a001

Reference yield:

methyl 5-methyl-2,4-hexadienoate (52148-91-1) → ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ6-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester (107302-10-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) diisopropylamine, n-butyllithium / 1.) THF, HMPA, -35 deg C, 15 min, 2.) THF, HMPA, 4 h

2: 97 percent / LiAlH₄ / diethyl ether / 1 h / Heating

3: 81 percent / diisopropylethylamine / CH₂Cl₂ / Ambient temperature

4: 30 percent / toluene / 3 h / Ambient temperature

5: 24 percent / K₂HPO₄, trifluoroperacetic acid / CH₂Cl₂ / -10 °C

6: 70 percent / conc. HCl / methanol / 4 h / 50 °C

With hydrogenchloride; dipotassium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; trifluoroacetyl peroxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo00383a001

Reference yield:

(E)-5-methylhexa-3,5-dien-1-ol (80719-84-2) → ((Z)-4-Methyl-2,2-dioxo-3,6,7,8-tetrahydro-2H-2λ6-[1,2]oxathiocin-6-yl)-carbamic acid benzyl ester (107302-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: 30 percent / toluene / 3 h / Ambient temperature

3: 24 percent / K₂HPO₄, trifluoroperacetic acid / CH₂Cl₂ / -10 °C

4: 70 percent / conc. HCl / methanol / 4 h / 50 °C

With hydrogenchloride; dipotassium hydrogenphosphate; trifluoroacetyl peroxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; toluene;

DOI:10.1021/jo00383a001

upstream raw materials:

3-(2-Methoxymethoxy-ethyl)-5-methyl-1,1-dioxo-3,6-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl ester

methyl 5-methyl-2,4-hexadienoate

(E)-5-methylhexa-3,5-dien-1-ol

(E)-methyl 5-methylhexa-3,5-dienoate

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