2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

Base Information

Chemical Name:2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose
CAS No.:316353-20-5
Molecular Formula:C₂₀H₂₉BrN₂O₈
Molecular Weight:505.363
Hs Code.:

Synonyms:2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

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Chemical Property of 2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

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Technology Process of 2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

There total 8 articles about 2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose 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: 39.0%

: 316353-16-9
Isopropyl-carbamic acid (2S,3R,4S,5R,6R)-3-benzylcarbamoyloxy-2-ethylsulfanyl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

: 540-51-2
2-bromoethanol

: 316353-20-5
2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo001099v

Reference yield:

: 121654-00-0
3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose

: 316353-20-5
2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / trifluoroacetic anhydride / toluene / 48 h / 20 °C

2: 62 percent / pyridine / CH₂Cl₂ / 120 h / Heating

3: 95 percent / aq. hydrofluoric acid / acetonitrile / 1 h / 20 °C

4: 50 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 5 h / 20 °C

5: 80 percent / copper(I) chloride / dimethylformamide / 12 h / 20 °C

6: 30 percent / borane-trimethylamine complex / tetrahydrofuran / 12 h / 20 °C

7: 39 percent / N-iodosuccinimide; trifluoromethanesulfoic acid / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylamine-borane; hydrogen fluoride; toluene-4-sulfonic acid; trifluoroacetic anhydride; copper(l) chloride; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo001099v

Reference yield:

: 3173-56-6
benzyl isothiocyanate

: 316353-20-5
2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 62 percent / pyridine / CH₂Cl₂ / 120 h / Heating

2: 95 percent / aq. hydrofluoric acid / acetonitrile / 1 h / 20 °C

3: 50 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 5 h / 20 °C

4: 80 percent / copper(I) chloride / dimethylformamide / 12 h / 20 °C

5: 30 percent / borane-trimethylamine complex / tetrahydrofuran / 12 h / 20 °C

6: 39 percent / N-iodosuccinimide; trifluoromethanesulfoic acid / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylamine-borane; hydrogen fluoride; toluene-4-sulfonic acid; copper(l) chloride; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo001099v