N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

Base Information

Chemical Name:N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide
CAS No.:246516-66-5
Molecular Formula:C₆₃H₇₆ClNO₂₂
Molecular Weight:1234.74
Hs Code.:

N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

Synonyms:N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

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Chemical Property of N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

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Technology Process of N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

There total 4 articles about N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide 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: 87.0%

: 1575-61-7
5-Chlorovaleroyl chloride

: acetic acid 5-acetoxy-6-acetoxymethyl-2-(4,5-diacetoxy-2-acetoxymethyl-6-amino-tetrahydro-pyran-3-yloxy)-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

: 246516-66-5
N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/ja990219h

Reference yield:

: 74801-29-9
phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

: 246516-66-5
N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 4 A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

1.2: 86 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 1 h / -30 °C

2.1: H₂ / PtO₂*H₂O / methanol / 2 h / 20 °C / 3040 Torr

3.1: 87 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

With 4 A molecular sieve; hydrogen; triethylamine; platinum(IV) oxide; In methanol; dichloromethane; 1.1: glycosylation / 1.2: glycosylation / 2.1: Reduction / 3.1: Acetylation;
DOI:10.1021/ja990219h

Reference yield:

: 226707-92-2
O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide

: 246516-66-5
N-[O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl]-5-chloropentamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 4 A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

1.2: 86 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 1 h / -30 °C

2.1: H₂ / PtO₂*H₂O / methanol / 2 h / 20 °C / 3040 Torr

3.1: 87 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

With 4 A molecular sieve; hydrogen; triethylamine; platinum(IV) oxide; In methanol; dichloromethane; 1.1: glycosylation / 1.2: glycosylation / 2.1: Reduction / 3.1: Acetylation;
DOI:10.1021/ja990219h