(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:220047-69-8
Molecular Formula:C₂₄H₃₁NO₆S
Molecular Weight:461.579
Hs Code.:

Synonyms:(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 12 articles about (2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 95.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 220047-66-5
((3R,4S,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol

: 220047-69-8
(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 3h; under 760 Torr; Ambient temperature;
DOI:10.1016/S0040-4020(98)00989-2

Reference yield:

: 175229-12-6
(R)-3-benzyloxy-2-(tert-butoxycarbonylamino)propyl phenyl sulfone

: 220047-69-8
(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / aq. HCl / ethyl acetate / 2 h / Ambient temperature

2: 1.) titanium(IV) isopropoxide, 2.) NaBH₃CN / 1.) EtOH, room temp., 1 h, 2.) EtOH, overnight

3: 63 percent / K₂CO₃ / dimethylformamide / 48 h / 80 °C

4: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature

5: 85 percent / pyridine / 24 h / 0 °C

6: 99 percent / K₂CO₃ / dimethylformamide; H₂O / 24 h / Ambient temperature

7: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C

8: 95 percent / H₂ / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(98)00989-2

Reference yield:

: 220047-57-4
((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

: 220047-69-8
(2R,3S,4R)-3-Benzenesulfonyl-2-benzyloxymethyl-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 63 percent / K₂CO₃ / dimethylformamide / 48 h / 80 °C

2: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature

3: 85 percent / pyridine / 24 h / 0 °C

4: 99 percent / K₂CO₃ / dimethylformamide; H₂O / 24 h / Ambient temperature

5: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C

6: 95 percent / H₂ / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; hydrogen; potassium hexamethylsilazane; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(98)00989-2