(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Base Information

Chemical Name:(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate
CAS No.:1292309-27-3
Molecular Formula:C₂₃H₂₉NO₈S
Molecular Weight:479.551
Hs Code.:

Synonyms:(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

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Chemical Property of (R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

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Technology Process of (R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

There total 7 articles about (R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 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: 93.0%

: 98-59-9
p-toluenesulfonyl chloride

: benzyl ((4R,5R)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

: 1292309-27-3
(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 0 - 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.01.021

Reference yield:

: 72551-02-1
2,3:4,5-Di-O-isopropylidene-1-O-methylsulfonyl-D-arabinitol

: 1292309-27-3
(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium azide / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

3: sodium carbonate / dichloromethane / 0 - 20 °C

4: water; acetic acid / 20 °C

5: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With sodium azide; palladium 10% on activated carbon; water; hydrogen; di(n-butyl)tin oxide; sodium carbonate; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2011.01.021

Reference yield:

: 19139-74-3
2,3:4,5-di-O-isopropylidene-D-arabinitol

: 1292309-27-3
(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: sodium azide / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

4.1: sodium carbonate / dichloromethane / 0 - 20 °C

5.1: water; acetic acid / 20 °C

6.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With sodium azide; palladium 10% on activated carbon; water; hydrogen; di(n-butyl)tin oxide; sodium carbonate; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2011.01.021