Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester
CAS No.:290334-85-9
Molecular Formula:C₂₆H₃₆O₇S
Molecular Weight:492.634
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

There total 8 articles about Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl 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: 65.0%

: 98-59-9
p-toluenesulfonyl chloride

: 290334-91-7
1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol

: 290334-85-9
Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Guidance literature:: With dmap; In pyridine; at 0 ℃; for 14h;
DOI:10.1016/S0040-4039(00)00749-8

Reference yield:

: 85325-93-5,105454-09-9,105454-10-2
1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol

: 290334-85-9
Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuCN / tetrahydrofuran / 0.5 h / -80 °C

1.2: 98 percent / tetrahydrofuran / 8 h / -80 °C

2.1: 95 percent / sodium hydride / tetrahydrofuran / 12 h / 20 °C

3.1: 2.01 g / CuCl₂*2H₂O / acetonitrile / 0.67 h / 0 °C

4.1: pyridine / CH₂Cl₂ / 24 h / 0 °C

With pyridine; sodium hydride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo0269058

Reference yield:

: 290836-45-2
6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol

: 290334-85-9
Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / CH₂Cl₂ / 10 h / -80 - -20 °C

2.1: 3.8 g / K₂CO₃ / methanol / 2 h / 20 °C

3.1: CuCN / tetrahydrofuran / 0.5 h / -80 °C

3.2: 98 percent / tetrahydrofuran / 8 h / -80 °C

4.1: 95 percent / sodium hydride / tetrahydrofuran / 12 h / 20 °C

5.1: 2.01 g / CuCl₂*2H₂O / acetonitrile / 0.67 h / 0 °C

6.1: pyridine / CH₂Cl₂ / 24 h / 0 °C

With pyridine; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo0269058