8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Base Information

• Chemical Name: 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside
• CAS No.: 180336-02-1
• Molecular Formula: C₅₄H₆₉NO₁₃
• Molecular Weight: 940.141

Synonyms:8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Chemical Property of 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

There total 7 articles about 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside 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: 96.0%

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide (77790-47-7) + 8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylopyranoside (180335-99-3) → 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside (180336-02-1)

Guidance literature:

With calcium sulfate; 4 A molecular sieve; mercury(II) cyanide; In nitromethane; toluene; for 2h;

DOI:10.1016/0008-6215(96)00047-X

Reference yield:

ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (71048-95-8) → 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside (180336-02-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / -50 - -40 °C

1.2: 68 percent / dimethylformamide / 1 h / -50 - 20 °C

2.1: 83 percent / HCl; sodium cyanoborohydride; 3 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 0.67 h / 0 °C

3.1: 73 percent / 4-dimethylaminopyridine / acetonitrile / 22 h / 20 °C / Heating

4.1: 90 percent / α,α'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 80 °C

5.1: 95 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 0.5 h

6.1: 96 percent / mercuric cyanide; calcium sulfate; 4 Angstroem molecular sieves / nitromethane; toluene / 2 h

With hydrogenchloride; dmap; calcium sulfate; ammonium cerium(IV) nitrate; 3 A molecular sieve; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; nitromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Metallation / 1.2: benzylation / 2.1: Ring cleavage / 3.1: Esterification / 4.1: Reduction / 5.1: debenzylation / 6.1: glycosylation;

DOI:10.1016/0008-6215(96)00047-X

Reference yield:

8-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside (152480-28-9) → 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside (180336-02-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / HCl; sodium cyanoborohydride; 3 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 0.67 h / 0 °C

2: 73 percent / 4-dimethylaminopyridine / acetonitrile / 22 h / 20 °C / Heating

3: 90 percent / α,α'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 80 °C

4: 95 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 0.5 h

5: 96 percent / mercuric cyanide; calcium sulfate; 4 Angstroem molecular sieves / nitromethane; toluene / 2 h

With hydrogenchloride; dmap; calcium sulfate; ammonium cerium(IV) nitrate; 3 A molecular sieve; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; mercury(II) cyanide; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; nitromethane; water; toluene; acetonitrile; 1: Ring cleavage / 2: Esterification / 3: Reduction / 4: debenzylation / 5: glycosylation;

DOI:10.1016/0008-6215(96)00047-X

upstream raw materials:

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

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylopyranoside

ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2,4-dideoxy-3-O-(4-methoxybenzyl)-β-D-xylopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

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