Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester
• CAS No.: 191163-54-9
• Molecular Formula: C₃₃H₃₆N₂O₉S
• Molecular Weight: 636.723
• Mol file: 191163-54-9.mol

Synonyms:Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester

Chemical Property of Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester

There total 18 articles about Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-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:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester (191163-54-9)

Guidance literature:

Multi-step reaction with 13 steps

1: tetrahydrofuran; diethyl ether / 2 h / 0 °C

2: TBAF / tetrahydrofuran / 1 h / Ambient temperature

3: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

4: aq. AcOH / 3 h / 90 °C

5: pyridine / 48 h / Ambient temperature

6: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

7: 95 percent / CH₃ONa / methanol / 16 h / Ambient temperature

8: 89 percent / pyridine / 1 h / Ambient temperature

9: aq. NaOH / 18 h / Heating

10: aq. NaHCO₃ / CH₂Cl₂

11: aq. NaIO₄, OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / Ambient temperature

12: aq. NaBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

13: pyridine / 20 h / Ambient temperature

With pyridine; benzenesulfonamide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

benzyl bromide (100-39-0) → Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester (191163-54-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

2: aq. AcOH / 3 h / 90 °C

3: pyridine / 48 h / Ambient temperature

4: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

5: 95 percent / CH₃ONa / methanol / 16 h / Ambient temperature

6: 89 percent / pyridine / 1 h / Ambient temperature

7: aq. NaOH / 18 h / Heating

8: aq. NaHCO₃ / CH₂Cl₂

9: aq. NaIO₄, OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / Ambient temperature

10: aq. NaBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

11: pyridine / 20 h / Ambient temperature

With pyridine; benzenesulfonamide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-α-D-ribofuranose (151426-67-4) → Toluene-4-sulfonic acid 2-[(2R,3S,4S,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-ethyl ester (191163-54-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

2: aq. AcOH / 3 h / 90 °C

3: pyridine / 48 h / Ambient temperature

4: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

5: 95 percent / CH₃ONa / methanol / 16 h / Ambient temperature

6: 89 percent / pyridine / 1 h / Ambient temperature

7: aq. NaOH / 18 h / Heating

8: aq. NaHCO₃ / CH₂Cl₂

9: aq. NaIO₄, OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / Ambient temperature

10: aq. NaBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

11: pyridine / 20 h / Ambient temperature

With pyridine; benzenesulfonamide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

upstream raw materials:

p-toluenesulfonyl chloride

1-[3,5-Di-O-benzyl-3-C-(2-hydroxyethyl)-β-D-arabinofuranosyl]thymine

benzyl bromide

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

Downstream raw materials:

(1S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

(1S,5R,6R,8R)-6-(4,4'-Dimethoxytrityloxymethyl)-5-hydroxy-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane