Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside

Base Information

• Chemical Name: Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside
• CAS No.: 150161-25-4
• Molecular Formula: C₃₆H₄₃NO₁₅
• Molecular Weight: 729.735
• Mol file: 150161-25-4.mol

Synonyms:

Chemical Property of Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside

There total 4 articles about Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside 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:

methyl 2,3-O-isopropylidene-α-D-mannopyranoside (63167-69-1) → Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside (150161-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 16 h / Ambient temperature

2: 80 percent / CF₃CO₂H, water / CHCl₃ / 1 h / Ambient temperature

3: 1) Bu₂SnO / 1) MeOH, 1 h, reflux, 2) DMF, 5 h, 110 deg C

4: 1) 4A molecular sieves, N-iodosuccinimide, 2) CF₃SO₃H / 1) CH₂Cl₂, 30 min, r.t., 2) 2 h, r.t.

With barium dihydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; water; di(n-butyl)tin oxide; trifluoroacetic acid; barium(II) oxide; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84079-L

Reference yield:

Methyl 2,3-O-isopropylidene-4,6-di-O-methyl-α-D-mannopyranoside (150161-23-2) → Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside (150161-25-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / CF₃CO₂H, water / CHCl₃ / 1 h / Ambient temperature

2: 1) Bu₂SnO / 1) MeOH, 1 h, reflux, 2) DMF, 5 h, 110 deg C

3: 1) 4A molecular sieves, N-iodosuccinimide, 2) CF₃SO₃H / 1) CH₂Cl₂, 30 min, r.t., 2) 2 h, r.t.

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; water; di(n-butyl)tin oxide; trifluoroacetic acid; In chloroform;

DOI:10.1016/0008-6215(93)84079-L

Reference yield:

Methyl 4,6-di-O-methyl-α-D-mannopyranoside (4153-25-7,13000-41-4,23262-68-2,23487-00-5,25029-39-4,35780-76-8,52554-55-9,82262-93-9) → Methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside (150161-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Bu₂SnO / 1) MeOH, 1 h, reflux, 2) DMF, 5 h, 110 deg C

2: 1) 4A molecular sieves, N-iodosuccinimide, 2) CF₃SO₃H / 1) CH₂Cl₂, 30 min, r.t., 2) 2 h, r.t.

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; di(n-butyl)tin oxide;

DOI:10.1016/0008-6215(93)84079-L

upstream raw materials:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Methyl 3-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside

Methyl 4,6-di-O-methyl-α-D-mannopyranoside

methyl 2,3-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3-O-acetyl-4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

4-Nitrophenyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(4,6-di-O-methyl-α-D-mannopyranosyl)-(1->6)-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4S,5R,6R)-4-benzyloxy-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester