thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

Base Information

Chemical Name:thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose
CAS No.:316353-18-1
Molecular Formula:C₃₅H₄₄N₂O₈S
Molecular Weight:652.809
Hs Code.:

Synonyms:thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

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Chemical Property of thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

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Technology Process of thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

There total 9 articles about thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-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: 86.0%

: 100-39-0
benzyl bromide

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

: 316353-18-1
thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo001099v

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 316353-18-1
thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 5 h / 20 °C

2: 80 percent / copper(I) chloride / dimethylformamide / 12 h / 20 °C

3: 56 percent / borane-trimethylamine complex / tetrahydrofuran / 12 h / 20 °C

4: 86 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

With trimethylamine-borane; sodium hydride; toluene-4-sulfonic acid; copper(l) chloride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo001099v

Reference yield:

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

: 316353-18-1
thioethyl 4-O-benzyl-2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-6-O-(4-methoxybenzyl)-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: 56 percent / borane-trimethylamine complex / tetrahydrofuran / 12 h / 20 °C

7: 86 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

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