Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 377079-34-0
• Molecular Formula: C₃₂H₃₄N₂O₉S
• Molecular Weight: 622.696
• Mol file: 377079-34-0.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 10 articles about Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl 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:

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (377079-34-0)

Guidance literature:

Multi-step reaction with 9 steps

1: NaIO₄

2: NaOH / H₂O

3: aq. HCOOH

4: pyridine

5: 70 percent / trimethylsilyl trifluoromethanesulfonate

6: 82 percent / MeONa

With pyridine; sodium hydroxide; sodium periodate; formic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In water;

DOI:10.1081/NCN-100002354

Reference yield:

3-C-(benzyloxymethyl)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (85315-67-9) → Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (377079-34-0)

Guidance literature:

Multi-step reaction with 10 steps

1: aq. AcOH

2: NaIO₄

3: NaOH / H₂O

4: aq. HCOOH

5: pyridine

6: 70 percent / trimethylsilyl trifluoromethanesulfonate

7: 82 percent / MeONa

With pyridine; sodium hydroxide; sodium periodate; formic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; In water;

DOI:10.1081/NCN-100002354

Reference yield:

(3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (149207-10-3) → Toluene-4-sulfonic acid (2S,3S,4R,5R)-2,3-bis-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (377079-34-0)

Guidance literature:

Multi-step reaction with 8 steps

1: NaOH / H₂O

2: aq. HCOOH

3: pyridine

4: 70 percent / trimethylsilyl trifluoromethanesulfonate

5: 82 percent / MeONa

With pyridine; sodium hydroxide; formic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In water;

DOI:10.1081/NCN-100002354

upstream raw materials:

p-toluenesulfonyl chloride

1-((2R,3R,4S,5R)-4,5-Bis-benzyloxymethyl-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

3-C-(benzyloxymethyl)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose