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

Base Information

Chemical Name: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
CAS No.:180336-03-2
Molecular Formula:C₅₂H₆₇NO₁₂
Molecular Weight:898.103
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 8 articles about 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 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: 93.0%

: 180336-02-1
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

: 180336-03-2
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

Guidance literature:: With sodium methylate; In methanol; for 24h;
DOI:10.1016/0008-6215(96)00047-X

Reference yield:

: 71048-95-8
ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 180336-03-2
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

Guidance literature:: Multi-step reaction with 7 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

7.1: 93 percent / NaOMe / methanol / 24 h

With hydrogenchloride; dmap; calcium sulfate; ammonium cerium(IV) nitrate; 3 A molecular sieve; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; 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 / 7.1: Deacetylation;
DOI:10.1016/0008-6215(96)00047-X

Reference yield:

: 152480-29-0
8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside

: 180336-03-2
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

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / 4-dimethylaminopyridine / acetonitrile / 22 h / 20 °C / Heating

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

3: 95 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 0.5 h

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

5: 93 percent / NaOMe / methanol / 24 h

With dmap; calcium sulfate; ammonium cerium(IV) nitrate; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; In methanol; nitromethane; water; toluene; acetonitrile; 1: Esterification / 2: Reduction / 3: debenzylation / 4: glycosylation / 5: Deacetylation;
DOI:10.1016/0008-6215(96)00047-X