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

Base Information

• Chemical Name: Toluene-4-sulfonic acid 3-[(2R,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester
• CAS No.: 1054635-79-8
• Molecular Formula: C₃₄H₃₈N₂O₉S
• Molecular Weight: 650.75
• Mol file: 1054635-79-8.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about Toluene-4-sulfonic acid 3-[(2R,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl 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: 58.0%

p-toluenesulfonyl chloride (98-59-9) + 1-[3,5-Di-O-benzyl-3-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine (199931-19-6) → 1-{3,5-Di-O-benzyl-2-O-(p-tolylsulfonyl)-3-C-[3-(p-tolylsulfonyloxy)propyl]-β-D-ribofuranosyl}thymine (201358-15-8) + Toluene-4-sulfonic acid 3-[(2R,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester (1054635-79-8)

Guidance literature:

With pyridine; at 0 ℃; for 2h; Yields of byproduct given;

Reference yield:

benzyl bromide (100-39-0) → Toluene-4-sulfonic acid 3-[(2R,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester (1054635-79-8)

Guidance literature:

Multi-step reaction with 7 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: 1.) BH₃*1,4-oxathiane, 2.) H₂O₂, aq. NaOH / 1.) THF, r.t., 45 min, 2.) r.t., 1 h

7: pyridine / 18 h / 0 °C

With pyridine; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; borane:1,4-oxathiane; dihydrogen peroxide; sodium methylate; sodium hydride; acetic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → Toluene-4-sulfonic acid 3-[(2R,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester (1054635-79-8)

Guidance literature:

Multi-step reaction with 9 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: 1.) BH₃*1,4-oxathiane, 2.) H₂O₂, aq. NaOH / 1.) THF, r.t., 45 min, 2.) r.t., 1 h

9: pyridine / 18 h / 0 °C

With pyridine; benzenesulfonamide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; borane:1,4-oxathiane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

p-toluenesulfonyl chloride

1-[3,5-Di-O-benzyl-3-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine

benzyl bromide

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

Downstream raw materials:

(1R,6R,7R,9R)-6-Benzyloxy-7-benzyloxymethyl-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane

(1R,6R,7R,9R)-7-(4,4'-Dimethoxytrityloxymethyl)-6-hydroxy-9-(thymin-1-yl)-2,8-dioxabicyclo[4.3.0]nonane