3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose

Base Information

• Chemical Name: 3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose
• CAS No.: 111820-09-8
• Molecular Formula: C₂₇H₃₅NO₁₇
• Molecular Weight: 645.571

Synonyms:3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose

Chemical Property of 3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose

Chemical Property:

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Technology Process of 3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose

There total 1 articles about 3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose 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: 27.0%

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3-di-O-acetyl-β-D-glucopyranoside (141243-54-1) + 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide (4753-07-5) → 3,6,2',3',4',6'-Hexa-O-acetyl-1,2-O-(2,3,2',3',4',6'-hexa-O-acetyl-1-O-benzyl-β-lactos-6-yl orthoacetyl)-α-lactose (141243-56-3) + 3,6-di-O-acetyl-1,2-O-<(exo and endo)>-1-cyanoethylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose (63306-31-0,111820-09-8,114717-22-5)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 40 ℃; for 5h;

DOI:10.1016/0008-6215(92)84058-Z

Reference yield: 75.0%

3,6-di-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose (111820-09-8) + Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-pent-4-enyloxy-2-trityloxymethyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (188806-82-8) → C66H81NO33 (188806-94-2)

Guidance literature:

With Cl⁽³⁾HO₄; In dichloromethane;

DOI:10.1016/S0040-4039(97)00106-8

Reference yield: 47.0%

3,6-di-O-acetyl-1,2-O-<(exo and endo)>-1-cyanoethylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose (63306-31-0,111820-09-8,114717-22-5) + N-9-fluorenylmethoxycarbonyl-O-trityl-L-serine benzyl ester (171820-92-1) → N-9-fluorenylmethoxycarbonyl-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl>-L-serine benzyl ester

Guidance literature:

With Cl⁽³⁾HO₄; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1016/0008-6215(95)00097-D

upstream raw materials:

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3-di-O-acetyl-β-D-glucopyranoside

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

Downstream raw materials:

C₆₆H₈₁NO₃₃

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