Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid

Base Information

• Chemical Name: Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid
• CAS No.: 146579-75-1
• Molecular Formula: C₅₁H₆₆O₁₁
• Molecular Weight: 855.078
• Mol file: 146579-75-1.mol

Synonyms:

Chemical Property of Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid

There total 6 articles about Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid 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: 99.0%

Octyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid (146579-74-0) → Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid (146579-75-1)

Guidance literature:

With ammonia; for 24h; Ambient temperature;

DOI:10.1016/0008-6215(92)85006-L

Reference yield:

4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-α-D-mannopyranosyl bromide (102728-52-9) → Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid (146579-75-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / silver acetate, molecular sieves 4 A

2: 2) HgO, HgCl₂ / 2)2>PF₆ / 1.) THF, r.t. 10 min., 2.) H₂O, acetone, 5 min.

3: NH₃/CH₃OH / 2 h / Ambient temperature

4: 4-toluenesulfonic acid / dimethylformamide / 0.33 h

5: 87 percent / molecular sieves 3 A, Me₃Si-triflate / CH₂Cl₂ / 0.17 h / Ambient temperature

6: 99 percent / methanol. NH₃ / 24 h / Ambient temperature

With methanol; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; ammonia; silver(I) acetate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)85006-L

Reference yield:

Octyl-4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosid (139493-93-9) → Octyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid (146579-75-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2) HgO, HgCl₂ / 2)2>PF₆ / 1.) THF, r.t. 10 min., 2.) H₂O, acetone, 5 min.

2: NH₃/CH₃OH / 2 h / Ambient temperature

3: 4-toluenesulfonic acid / dimethylformamide / 0.33 h

4: 87 percent / molecular sieves 3 A, Me₃Si-triflate / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 99 percent / methanol. NH₃ / 24 h / Ambient temperature

With methanol; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; ammonia; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)85006-L

upstream raw materials:

Octyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid

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

Octyl-2-O-benzyl-4,6-O-isopropyliden-β-D-mannopyranosid

Octyl-4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosid

Downstream raw materials:

Octyl-O-(3,4,6-tri-O-benzyl-2-O-methyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-β-mannopyranosid

Octyl-O-(3,4,6-tri-O-benzyl-2-O-methyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid