phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside
• CAS No.: 400091-21-6
• Molecular Formula: C₂₉H₃₆O₇S
• Molecular Weight: 528.667
• Mol file: 400091-21-6.mol

Synonyms:phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside

There total 12 articles about phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside 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: 93.0%

acetic anhydride (108-24-7) + phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside (400091-16-9) → phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside (400091-21-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside (400091-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / TsOH*H₂O / tetrahydrofuran / 2 h / 25 °C

2: 96 percent / DMAP; Et₃N / CH₂Cl₂ / 16 h / Heating

3: 77 percent / NaBH₃CN; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

4: 82 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 25 °C

5: 93 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 25 °C

With hydrogenchloride; dmap; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q

Reference yield:

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside (144985-19-3) → phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside (400091-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / TsOH*H₂O / tetrahydrofuran / 2 h / 25 °C

2: 96 percent / DMAP; Et₃N / CH₂Cl₂ / 16 h / Heating

3: 77 percent / NaBH₃CN; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

4: 82 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 25 °C

5: 93 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 25 °C

With hydrogenchloride; dmap; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q

upstream raw materials:

acetic anhydride

phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

4-methoxyphenyl 4-O-(4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl)-3-O-allyl-6-O-benzyl-2-O-pivaloyl-β-D-galactopyranoside