allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside
• CAS No.: 158382-62-8
• Molecular Formula: C₇₅H₉₁NO₁₇
• Molecular Weight: 1278.54
• Mol file: 158382-62-8.mol

Synonyms:allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside

Chemical Property of allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside

There total 10 articles about allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside 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: 48.0%

(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran (107802-80-2) + allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside (158382-61-7) → allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside (158382-62-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/hlca.19940770211

Reference yield:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) → allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside (158382-62-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / CH₂Cl₂; pyridine / 2 h / 0 °C

2: CH₂Cl₂; pyridine / 2 h / 0 °C

3: H₂O / pyridine; CH₂Cl₂ / 4 h / Heating

4: 52 percent / mol. sieves 4A, BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

5: 51 percent / guanidine / CH₂Cl₂; ethanol / 4 h

6: 48 percent / mol. sieves 4A, NIS, TfOH / CH₂Cl₂; diethyl ether / 3 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; water; guanidine nitrate; In pyridine; diethyl ether; ethanol; dichloromethane;

DOI:10.1002/hlca.19940770211

Reference yield:

O-(2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate (130177-78-5) → allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl)-α-L-fucopyranosyl)-β-D-galactopyranosyl-β-D-galactopyranoside (158382-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / mol. sieves 4A, BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

2: 51 percent / guanidine / CH₂Cl₂; ethanol / 4 h

3: 48 percent / mol. sieves 4A, NIS, TfOH / CH₂Cl₂; diethyl ether / 3 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; guanidine nitrate; In diethyl ether; ethanol; dichloromethane;

DOI:10.1002/hlca.19940770211

upstream raw materials:

(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran

allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-3-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

O-(2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate

Downstream raw materials:

allyl 2-acetamido-2-deoxy-3-O-<3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-β-D-galactopyranoside