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

Base Information

Chemical Name:Isopropyl-carbamic acid (2S,3R,4S,5R,6R)-3-benzylcarbamoyloxy-2-ethylsulfanyl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
CAS No.:316353-16-9
Molecular Formula:C₂₀H₃₀N₂O₇S
Molecular Weight:442.533
Hs Code.:

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

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Chemical Property of Isopropyl-carbamic acid (2S,3R,4S,5R,6R)-3-benzylcarbamoyloxy-2-ethylsulfanyl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

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Technology Process of Isopropyl-carbamic acid (2S,3R,4S,5R,6R)-3-benzylcarbamoyloxy-2-ethylsulfanyl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

There total 7 articles about Isopropyl-carbamic acid (2S,3R,4S,5R,6R)-3-benzylcarbamoyloxy-2-ethylsulfanyl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl 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: 56.0%

: 316353-13-6
thioethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranose

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

: 316353-14-7
thioethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: With trimethylamine-borane; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/jo001099v

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 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

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

Guidance literature:: Multi-step reaction with 5 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

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