phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside

Base Information

• Chemical Name: phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside
• CAS No.: 335197-20-1
• Molecular Formula: C₁₉H₃₀O₅SSi
• Molecular Weight: 398.596
• Mol file: 335197-20-1.mol

Synonyms:phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside

Chemical Property of phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside

There total 8 articles about phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside 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: 90.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + phenyl 2-O-acetyl-1-thio-1-deoxy-α-L-arabinopyranoside (321125-10-4) → phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside (335197-20-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -70 - -60 ℃; for 2h;

DOI:10.1021/ja004098t

Reference yield:

1,2,3,4-tetra-O-acetyl-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,142130-89-0,123163-97-3) → phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside (335197-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / SnCl₄ / CH₂Cl₂ / 6 h / -78 °C

2: 95 percent / NaOMe / methanol / 6 h / 25 °C

3: CSA / CH₂Cl₂ / 12 h / 25 °C

4: DMAP; Et₃N / CH₂Cl₂ / 2 h / 25 °C

5: 5.1 g / Amberlite IR-118H / methanol / 12 h / 25 °C

6: 90 percent / lutidine / CH₂Cl₂ / 2 h / -70 - -60 °C

With dmap; Amberlite IR-118H; lutidine; camphor-10-sulfonic acid; sodium methylate; tin(IV) chloride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja012119t

Reference yield:

phenyl 3,4-O-isopropylidene-1-thio-α-L-arabinopyranoside (153984-54-4) → phenyl 2-O-acetyl-4-O-triethylsilyl-1-thio-1-deoxy-α-L-arabinopyranoside (335197-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP; Et₃N / CH₂Cl₂ / 2 h / 25 °C

2: 5.1 g / Amberlite IR-118H / methanol / 12 h / 25 °C

3: 90 percent / lutidine / CH₂Cl₂ / 2 h / -70 - -60 °C

With dmap; Amberlite IR-118H; lutidine; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja012119t

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

phenyl 2-O-acetyl-1-thio-1-deoxy-α-L-arabinopyranoside

1,2,3,4-tetra-O-acetyl-L-arabinopyranose

thiophenol

Downstream raw materials:

3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside}

4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

C₇₇H₁₁₆O₁₈Si₂

C₇₇H₁₁₆O₁₈Si₂