allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside
• CAS No.: 685104-22-7
• Molecular Formula: C₅₆H₅₈O₂₃
• Molecular Weight: 1099.06
• Mol file: 685104-22-7.mol

Synonyms:allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside

Chemical Property of allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside

There total 10 articles about allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside 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: 61.0%

allyl 4-O-acetyl-6-O-triphenylmethyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside (685104-21-6) → allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside (685104-22-7)

Guidance literature:

With acetic acid; at 50 ℃; for 4h;

DOI:10.1002/ejoc.200300580

Reference yield:

allyl 4,6-O-benzylidene-α-D-glucopyranoside (93382-48-0) → allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside (685104-22-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 58 percent / pyridine / 0 °C

2: 99 percent / imidazole; DMAP / dimethylformamide

3: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: 97 percent / molecular sieves 4 Angstroem; NIS; AgOTf / CH₂Cl₂; toluene / -15 - 20 °C

5: 83 percent / HF; pyridine / 20 °C

6: 100 percent / molecular sieves 4 Angstroem; NIS; AgOTf / CH₂Cl₂; toluene / -20 - 20 °C

7: 77 percent / HOAc / 70 °C

8: 92 percent / pyridine / 2 h / 80 °C

9: 100 percent / pyridine / 20 °C

10: 61 percent / HOAc / 4 h / 50 °C

With pyridine; 1H-imidazole; dmap; N-iodo-succinimide; 4 A molecular sieve; hydrogen fluoride; silver trifluoromethanesulfonate; diisobutylaluminium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.200300580

Reference yield:

ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-galactopyranoside → allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside (685104-22-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / molecular sieves 4 Angstroem; NIS; AgOTf / CH₂Cl₂; toluene / -15 - 20 °C

2: 83 percent / HF; pyridine / 20 °C

3: 100 percent / molecular sieves 4 Angstroem; NIS; AgOTf / CH₂Cl₂; toluene / -20 - 20 °C

4: 77 percent / HOAc / 70 °C

5: 92 percent / pyridine / 2 h / 80 °C

6: 100 percent / pyridine / 20 °C

7: 61 percent / HOAc / 4 h / 50 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; hydrogen fluoride; silver trifluoromethanesulfonate; acetic acid; In dichloromethane; toluene;

DOI:10.1002/ejoc.200300580

upstream raw materials:

allyl 4-O-acetyl-6-O-triphenylmethyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside

allyl 4,6-O-benzylidene-α-D-glucopyranoside

allyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside

allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Downstream raw materials:

tert-butyl [allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside]uronate