ChemicalBook CAS DataBase List Benzyl 2-Acetamido-4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl--D-galactosyl)-2-deoxy-a-D-galactopyranoside

Benzyl 2-Acetamido-4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl--D-galactosyl)-2-deoxy-a-D-galactopyranoside synthesis

7synthesis methods

Product Name:Benzyl 2-Acetamido-4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl--D-galactosyl)-2-deoxy-a-D-galactopyranoside
CAS Number:3809-10-7
Molecular formula:C33H43NO17
Molecular Weight:725.69

108-24-7
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90754-57-7 Synthesis

Benzyl2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-2-deoxy-a-D-galactopyranoside

90754-57-7
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Benzyl 2-Acetamido-4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl--D-galactosyl)-2-deoxy-a-D-galactopyranoside

3809-10-7
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$95.00/10mg

Yield:3809-10-7 98%

Reaction Conditions:

with pyridine at 20;

Steps:

13 3.13 Benzyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside (14)

A solution of 12 (200mg, 0.31mmol) in a mixture of dry pyridine (1mL) and Ac₂O (1mL) was stirred overnight at rt, ethanol (10mL) and toluene (10mL) was added and the reaction mixture was evaporated to dryness. The syrupy residue was subjected to column chromatography (toluene→acetone) affording 14 as a foam (220mg, 98%): R_f 0.5 (toluene/EtOAc 2:1); [α]_D²⁰+85.3; HRESIMS: m/z=726.2613 [M+H]⁺, calcd for C₃₃H₄₃NO₁₇: 725.2531; m/z=748.2425 [M+Na]⁺, calcd for C₃₃H₄₃NO₁₇Na: 748.2429; ¹H NMR (Gal=II, GalNAc=I): δ 7.40-7.30 (m, 5H, H₂h); 5.64 (d, 1H, J 9.0Hz, NH); 5.38 (bd, 1H, J_3,4 3.0Hz, H-4^I); 5.34 (bd, 1H, J_3,4 3,6Hz, H-4^II); 5.12 (dd, 1H, J_2,1 8.40Hz, J_2,3 10.2Hz, H-2^II); 5.04 (d, 1H, J_1,2 4.2Hz, H-1^I); 4.95 (dd, 1H, J_3,4 3.6Hz, J_2,3 10.2Hz, H-3^II); 4.58 (d, 1H, J_1,2 8.4Hz, H-1^II); 4.55-4.51 (m, 1H, H-2^I); 4.20-4.10 (m, 3H, H-5^I, H-6′^I, H-6^II); 4.04-4.01 (m, 1H, H-6^I); 4.00 (dd, 1H, J_3,4 3.0Hz, J_3,2 11.4Hz, H-3^I); 3.86-3.85 (m, 1H, H-5^II); 2.14-1.96 (m, 21H, COCH₃, NHCOCH₃); ¹³ NMR: δ 100.5 (C-1^II), 97.2 (C-1^I), 72.8 (C-3^I), 71.0 (C-5^I), 70.9 (C-3^II), 70.8 (CH₂Ph), 68.8 (C-4^I), 68.5 (C-2^II), 67.6 (C-5^I), 66.8 (C-4^II), 62.9 (C-6^I), 61.1 (C-6^II), 48.5 (C-2^I), 23.3 (NHCOCH₃), 20.5 (COCH₃).