Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester
CAS No.:191792-38-8
Molecular Formula:C₁₉H₂₂O₆S
Molecular Weight:378.446
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

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Chemical Property of Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

There total 10 articles about Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-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:

: 191792-37-7
Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

: 191792-38-8
Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: With tetrafluoroboric acid; In acetonitrile; for 2h; Ambient temperature;
DOI:10.1016/S0957-4166(97)00136-5

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 191792-38-8
Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 36percent aq. HCl / 0.5 h / Ambient temperature

2: 85 percent / TsCl, pyridine / -15 °C / 1.) -15 deg C, 1.5 h, 2.) RT, 2 d

3: 95 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min, 2.) RT, 3 d

4: 90 percent / aq. HgCl₂, HgO / acetonitrile / 1 h / Ambient temperature

5: 93 percent / 10 M BH₃*Me₂S / diethyl ether / 2 h / Ambient temperature

6: 48 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

7: 0.24 g / NaH, Bu₄NI / tetrahydrofuran / 16 h / Ambient temperature

8: 0.13 g / TBAF / tetrahydrofuran / 3 h / -10 °C

9: 0.12 g / pyridine / 48 h / Ambient temperature

10: 48percent aq. HBF₄ / acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; tetrafluoroboric acid; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; p-toluenesulfonyl chloride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0957-4166(97)00136-5

Reference yield:

: 61329-59-7
D-xylose diisobutyl dithioacetal

: 191792-38-8
Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / TsCl, pyridine / -15 °C / 1.) -15 deg C, 1.5 h, 2.) RT, 2 d

2: 95 percent / imidazole / dimethylformamide / 1.) 0 deg C, 30 min, 2.) RT, 3 d

3: 90 percent / aq. HgCl₂, HgO / acetonitrile / 1 h / Ambient temperature

4: 93 percent / 10 M BH₃*Me₂S / diethyl ether / 2 h / Ambient temperature

5: 48 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

6: 0.24 g / NaH, Bu₄NI / tetrahydrofuran / 16 h / Ambient temperature

7: 0.13 g / TBAF / tetrahydrofuran / 3 h / -10 °C

8: 0.12 g / pyridine / 48 h / Ambient temperature

9: 48percent aq. HBF₄ / acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; tetrafluoroboric acid; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; p-toluenesulfonyl chloride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0957-4166(97)00136-5