(R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

Base Information

Chemical Name:(R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide
CAS No.:1648743-85-4
Molecular Formula:C₂₅H₂₄N₂O₄S
Molecular Weight:448.543
Hs Code.:

Synonyms:(R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

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Chemical Property of (R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

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Technology Process of (R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

There total 8 articles about (R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-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: 70.0%

: 958264-13-6
benzyl N-(2,2-diphenylpent-4-en-1-yl)sulfamoylcarbamate

: 1648743-85-4
(R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

Guidance literature:: benzyl N-(2,2-diphenylpent-4-en-1-yl)sulfamoylcarbamate; With (R)-2-((2-diacetoxyiodophenyl)(methoxy)methyl)pyridine; In acetonitrile; at -48 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile; at -48 ℃; for 5h; Reagent/catalyst; enantioselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1002/chem.201403891

Reference yield:

: 958264-13-6
benzyl N-(2,2-diphenylpent-4-en-1-yl)sulfamoylcarbamate

: 1648743-85-4
(R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

: 1648743-86-5
(S)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

Guidance literature:: benzyl N-(2,2-diphenylpent-4-en-1-yl)sulfamoylcarbamate; With (R)-2-((2-diacetoxyiodophenyl)(methoxy)methyl)pyridine; In acetonitrile; at -48 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile; at -48 ℃; for 5h; Overall yield = 60 %; enantioselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1002/chem.201403891

Reference yield:

: 5558-71-4
2,2-diphenyl-pent-4-enenitrile

: 1648743-85-4
(R)-benzyl 5,5-diphenyltetrahydropyrrolo[1,2-b][1,2,5]thiadiazole-2(3H)-carboxylate-1,1-dioxide

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 16 h / 0 - 25 °C / Inert atmosphere; Schlenk technique

2.1: dichloromethane / Inert atmosphere; Schlenk technique

3.1: (R)-2-((2-diacetoxyiodophenyl)(methoxy)methyl)pyridine / acetonitrile / 0.08 h / -48 °C / Inert atmosphere; Schlenk technique

3.2: 5 h / -48 °C / Inert atmosphere; Schlenk technique

With lithium aluminium tetrahydride; (R)-2-((2-diacetoxyiodophenyl)(methoxy)methyl)pyridine; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1002/chem.201403891