benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 114079-16-2
• Molecular Formula: C₆₃H₆₆O₁₂
• Molecular Weight: 1015.21

Synonyms:benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 13 articles about benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-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: 16.0%

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (67831-42-9) + Acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yl ester (114967-54-3) → benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (114079-17-3) + benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (114079-16-2)

Guidance literature:

With 4 A molecular sieve; phenylselenyl triflate; In toluene; at -40 ℃; for 0.5h;

DOI:10.1016/0008-6215(90)84078-9

Reference yield:

2,2,2-trichloroethyl α-D-mannopyranoside (81555-82-0) → benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (114079-16-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 46 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 16 h / Ambient temperature

2: 70 percent / NaH / dimethylformamide / 16 h / -40 deg C to room temperature

3: 67 percent / aq. AcOH / 1 h / 90 °C

4: 1) bis(tri-n-butyltin) oxide, 2) tetra-n-butylammonium bromide / 1) toluene, 3 h, reflux, 2) 90 deg C, 16 h

5: 93 percent / pyridine / 16 h / Ambient temperature

6: 95 percent / zinc, AcOH / tetrahydrofuran / 8 h / Ambient temperature

7: 81 percent / pyridine / CH₂Cl₂ / 16 h / Ambient temperature

8: satd. HBr in dichloromethane / CH₂Cl₂ / 1 h / 0 deg C to room temperature

9: silver silicate, molecular sieves 4A / CH₂Cl₂ / 16 h / -50 deg C to room temperature

With pyridine; silver silicate; 4 A molecular sieve; tetrabutylammomium bromide; hydrogen bromide; sodium hydride; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb1961.54.2931

Reference yield:

benzyl bromide (100-39-0) → benzyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (114079-16-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) bis(tri-n-butyltin) oxide, 2) tetra-n-butylammonium bromide / 1) toluene, 3 h, reflux, 2) 90 deg C, 16 h

2: 93 percent / pyridine / 16 h / Ambient temperature

3: 95 percent / zinc, AcOH / tetrahydrofuran / 8 h / Ambient temperature

4: 81 percent / pyridine / CH₂Cl₂ / 16 h / Ambient temperature

5: satd. HBr in dichloromethane / CH₂Cl₂ / 1 h / 0 deg C to room temperature

6: silver silicate, molecular sieves 4A / CH₂Cl₂ / 16 h / -50 deg C to room temperature

With pyridine; silver silicate; 4 A molecular sieve; tetrabutylammomium bromide; hydrogen bromide; acetic acid; bis(tri-n-butyltin)oxide; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1271/bbb1961.54.2931

upstream raw materials:

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

Acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methylsulfanyl-tetrahydro-pyran-3-yl ester

4-O-acetyl-2,3,6-tri-O-benzyl-α-D-mannopyranosyl bromide

C₄₀H₄₀O₆S

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