phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid

Base Information

• Chemical Name: phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid
• CAS No.: 850637-28-4
• Molecular Formula: C₂₆H₂₄O₇S
• Molecular Weight: 480.538
• Mol file: 850637-28-4.mol

Synonyms:phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid

Chemical Property of phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid

There total 12 articles about phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid 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: 83.0%

phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside (398488-13-6) → phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid (850637-28-4)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; water; for 0.5h;

DOI:10.1021/ja045613g

Reference yield:

Benzoic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid (850637-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.50 g / aq. TFA / CH₂Cl₂ / 2 h

2: 83 percent / TEMPO; [bis(acetoxy)iodo]benzene / CH₂Cl₂; H₂O / 0.5 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; trifluoroacetic acid; In dichloromethane; water;

DOI:10.1021/ja045613g

Reference yield:

thiophenol (108-98-5) → phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid (850637-28-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 - 20 °C

2: KOtBu / CH₂Cl₂; methanol

3: p-TsOH / acetonitrile; dimethylformamide / 4 h / 50 °C

4: pyridine / toluene

5: 2.50 g / aq. TFA / CH₂Cl₂ / 2 h

6: 83 percent / TEMPO; [bis(acetoxy)iodo]benzene / CH₂Cl₂; H₂O / 0.5 h

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; potassium tert-butylate; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja045613g

upstream raw materials:

phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside

thiophenol

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate)

C₅₆H₅₃Cl₄NO₁₄S

C₅₄H₅₂Cl₃NO₁₃S

C₅₁H₅₁NO₁₁S