(R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:120191-68-6
Molecular Formula:C₂₂H₂₇NO₉
Molecular Weight:449.458
Hs Code.:

Synonyms:

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Chemical Property of (R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 10 articles about (R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-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:

: 115438-65-8
3,5-O-benzylidene-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octose

: 120191-68-6
(R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / triethylamine / CH₂Cl₂ / 0.75 h

2: 96 percent / sodium azide / dimethylformamide / 1 h / 90 °C

3: 64 percent / N-bromosuccinimide, barium carbonate, benzoyl peroxide / CCl₄ / 2 h / Ambient temperature

4: 91 percent / sodium methoxide / methanol / 1 h / Ambient temperature

5: 1.) tin(II) chloride, 2.) sodium acetate, 3.) sodium bicarbonate / 1.) methanol, 60 deg C, 1 h, 2.) ethanol, reflux, overnight, 3.) aqueous ethanol, 0 deg C, 3 h

6: 65 percent / 80percent aqueous acetic acid / 30 h / 80 - 90 °C

7: pyridine

With N-Bromosuccinimide; sodium azide; Perbenzoic acid; sodium acetate; sodium hydrogencarbonate; acetic acid; triethylamine; barium carbonate; tin(ll) chloride; sodium methylate; In pyridine; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89804-5

Reference yield:

: 115438-63-6
(E)-3-((3aR,3bS,7R,7aR,8aR)-2,2-Dimethyl-5-phenyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-acrylic acid ethyl ester

: 120191-68-6
(R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / hydrogen / 10percent palladium on charcoal / ethanol / 1.5 h

2: 93 percent / lithium aluminium hydride / diethyl ether / 1 h / Ambient temperature

3: 92 percent / triethylamine / CH₂Cl₂ / 0.75 h

4: 96 percent / sodium azide / dimethylformamide / 1 h / 90 °C

5: 64 percent / N-bromosuccinimide, barium carbonate, benzoyl peroxide / CCl₄ / 2 h / Ambient temperature

6: 91 percent / sodium methoxide / methanol / 1 h / Ambient temperature

7: 1.) tin(II) chloride, 2.) sodium acetate, 3.) sodium bicarbonate / 1.) methanol, 60 deg C, 1 h, 2.) ethanol, reflux, overnight, 3.) aqueous ethanol, 0 deg C, 3 h

8: 65 percent / 80percent aqueous acetic acid / 30 h / 80 - 90 °C

9: pyridine

With N-Bromosuccinimide; lithium aluminium tetrahydride; sodium azide; Perbenzoic acid; hydrogen; sodium acetate; sodium hydrogencarbonate; acetic acid; triethylamine; barium carbonate; tin(ll) chloride; palladium on activated charcoal; sodium methylate; In pyridine; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89804-5

Reference yield:

: 115438-64-7
ethyl 3,5-O-benzylidene-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-octuronate

: 120191-68-6
(R)-2-((2R,3S,4R,5R)-3,4,5-Triacetoxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / lithium aluminium hydride / diethyl ether / 1 h / Ambient temperature

2: 92 percent / triethylamine / CH₂Cl₂ / 0.75 h

3: 96 percent / sodium azide / dimethylformamide / 1 h / 90 °C

4: 64 percent / N-bromosuccinimide, barium carbonate, benzoyl peroxide / CCl₄ / 2 h / Ambient temperature

5: 91 percent / sodium methoxide / methanol / 1 h / Ambient temperature

6: 1.) tin(II) chloride, 2.) sodium acetate, 3.) sodium bicarbonate / 1.) methanol, 60 deg C, 1 h, 2.) ethanol, reflux, overnight, 3.) aqueous ethanol, 0 deg C, 3 h

7: 65 percent / 80percent aqueous acetic acid / 30 h / 80 - 90 °C

8: pyridine

With N-Bromosuccinimide; lithium aluminium tetrahydride; sodium azide; Perbenzoic acid; sodium acetate; sodium hydrogencarbonate; acetic acid; triethylamine; barium carbonate; tin(ll) chloride; sodium methylate; In pyridine; methanol; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89804-5