(αR^*,3R^*,4S^*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

Base Information

• Chemical Name: (αR^*,3R^*,4S^*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide
• CAS No.: 130274-76-9
• Molecular Formula: C₁₆H₁₇NO₃S
• Molecular Weight: 303.382

Synonyms:(αR^*,3R^*,4S^*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

Chemical Property of (αR^*,3R^*,4S^*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

Chemical Property:

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Technology Process of (αR^*,3R^*,4S^*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

There total 4 articles about (αR^*,3R^*,4S^*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide 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: 44.0%

(3R*,4S*)-4-Benzoyl-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (130274-73-6) → (αR*,3R*,4S*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (130274-76-9) + (αS*,3R*,4S*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (130324-18-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 0.333333h; Ambient temperature;

Reference yield: 11.0%

(RS)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (94287-18-0) + benzaldehyde (100-52-7) → (αR*,3R*,4S*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (130274-76-9) + (αS*,3R*,4S*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (130324-18-4) + N-methyl-1-<1-(α-hydroxybenzyl)-2-phenylvinylsulfonyl>methansulfonamide (137462-11-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

DOI:10.1002/ardp.2503241002

Reference yield:

benzoic acid ethyl ester (93-89-0,99341-95-4) → (αR*,3R*,4S*)-4-(α-hydroxybenzyl)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide (130274-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LDA / 1) THF, -78 deg C, 1 min 2) r.t., 2 h

2: 34 percent / NaBH₄ / ethanol / 0.33 h / Ambient temperature

With sodium tetrahydroborate; lithium diisopropyl amide; In ethanol;

upstream raw materials:

(3R*,4S*)-4-Benzoyl-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

(RS)-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

benzaldehyde

benzoic acid ethyl ester

Downstream raw materials:

(E)-4-benzylidene-2-methyl-3-phenyl-1,2-thiazetidine 1,1-dioxide

(αRS,3RS,4SR)-(2-methyl-3-phenyl-1,2-thiazetidin-4-yl)(phenyl)-methyl methanesulfonate 1,1-dioxide

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