benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside

Base Information

• Chemical Name: benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside
• CAS No.: 88830-29-9
• Molecular Formula: C₄₇H₄₈O₁₁
• Molecular Weight: 788.892
• Mol file: 88830-29-9.mol

Synonyms:

Chemical Property of benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside

There total 20 articles about benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside 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: 75.0%

benzoyl chloride (98-88-4) + benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside (88819-15-2) → benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside (88830-29-9)

Guidance literature:

With toluene-4-sulfonic acid; triethylamine; orthobenzoic acid trimethyl ester; 1.) DMF, 6 h, room temp.; 2.) pyridine, 2 h, room temp.;

DOI:10.1016/0008-6215(83)84006-3

Reference yield:

benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose (26623-26-7) → benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside (88830-29-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / methanol / 1.) r.t., 20 min; 2.) reflux, 10 min

2: 1.) RuO₄; 2.) NaBH₄ / 2.) MeOH

3: 92 percent / 1 M NaOMe / CH₂Cl₂; methanol / 5 h / Ambient temperature

4: 86 percent / NaH / dimethylformamide

5: 92 percent / water / acetic acid / 1 h / 80 °C

6: 53 percent / dibutyltin oxide, tetrabutylammonium bromide / benzene / 23 h / Heating

7: 1.) mercuric cianide, 2.) 1 M NaOMe / 1.) benzene-nitromethane, 45 deg C; 2.) CH₃OH, room temp.

8: 75 percent / trimethyl orthobenzoate, p-toluenesulfonic acid, Et₃N / 1.) DMF, 6 h, room temp.; 2.) pyridine, 2 h, room temp.

With sodium tetrahydroborate; ruthenium tetroxide; tetrabutylammomium bromide; water; sodium methylate; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; orthobenzoic acid trimethyl ester; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0008-6215(83)84006-3

Reference yield:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside (88830-29-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) potassium periodate, potassium carbonate, RhO₂; 2.) 2-propanol / 1.) 7 h, r.t.; 2.) r.t., 20 min

2: NaBH₄ / methanol / 1.) r.t., 20 min; 2.) reflux, 10 min

3: 86 percent / NaH / dimethylformamide

4: 92 percent / water / acetic acid / 1 h / 80 °C

5: 53 percent / dibutyltin oxide, tetrabutylammonium bromide / benzene / 23 h / Heating

6: 1.) mercuric cianide, 2.) 1 M NaOMe / 1.) benzene-nitromethane, 45 deg C; 2.) CH₃OH, room temp.

7: 75 percent / trimethyl orthobenzoate, p-toluenesulfonic acid, Et₃N / 1.) DMF, 6 h, room temp.; 2.) pyridine, 2 h, room temp.

With rhodium(IV) oxide; sodium tetrahydroborate; potassium metaperiodate; tetrabutylammomium bromide; water; sodium methylate; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; isopropyl alcohol; orthobenzoic acid trimethyl ester; In methanol; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0008-6215(83)84006-3

upstream raw materials:

benzoyl chloride

benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

benzyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside

Downstream raw materials:

benzyl O-(3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(3-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-(1->3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside

benzyl O-(4-O-benzoyl-2,3-di-O-methyl-α-L-fucopyranosyl)-(1->4)-O-(2,3-di-O-methyl-α-L-fucopyranosyl)-(1->3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-6-deoxy-α-L-talopyranoside