methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside
• CAS No.: 114869-96-4
• Molecular Formula: C₄₂H₄₈ClNO₁₆
• Molecular Weight: 858.293
• Mol file: 114869-96-4.mol

Synonyms:methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Chemical Property of methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

There total 17 articles about methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside 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:

methyl 2-O-acetyl-3-O-benzyl-4-O-(chloroacetyl)-2-O-acetyl-L-idopyranuronate trichloroacetimidate + C24H29NO8 → methoxy-[methyl-2-O-acetyl-3-O-benzyl-(4-chloroacetyl)-L-idofuranuranuate]-(1→4)-O-6-O-acetyl-2-benzylformate-2-deoxy-β-D-glucopyranoside + methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-96-4)

Guidance literature:

methyl 2-O-acetyl-3-O-benzyl-4-O-(chloroacetyl)-2-O-acetyl-L-idopyranuronate trichloroacetimidate; C₂₄H₂₉NO₈; In dichloromethane; toluene; at 21 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; for 1h; Overall yield = 40 %;

DOI:10.1039/c4ra17050d

Reference yield:

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / CH₂Cl₂ / Heating

2: 1) 2,6-dimethylpyridinium perchlorate / 1) chlorobenzene, 20 min, reflux, 2) reflux, 15 min

With 2,6-lutidinium perchlorate; In dichloromethane;

DOI:10.1016/0008-6215(87)80268-9

Reference yield:

methyl 3-O-benzyl-L-idopyranosyluronate (87326-77-0,87326-78-1) → methoxy-[methyl-2-O-acetyl-3-O-benzyl-(4-chloroacetyl)-L-idofuranuranuate]-(1→4)-O-6-O-acetyl-2-benzylformate-2-deoxy-β-D-glucopyranoside + methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-96-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; pyridine / dichloromethane / 10 h / -40 °C

2.1: titanium(IV) bromide / dichloromethane / 2 h / 30 °C

3.1: 2,4,6-trimethyl-pyridine / dichloromethane / 48 h / 30 °C

4.1: sodium methylate / methanol / 0 - 5 °C

5.1: pyridine / dichloromethane / 12 h / -20 - 0 °C / Inert atmosphere

6.1: acetic acid / water / 0.5 h / 28 °C

7.1: potassium carbonate / dichloromethane

8.1: dichloromethane; toluene / 0.5 h / 21 °C / Molecular sieve

8.2: 1 h

With pyridine; 2,4,6-trimethyl-pyridine; dmap; sodium methylate; titanium(IV) bromide; potassium carbonate; acetic acid; In methanol; dichloromethane; water; toluene;

DOI:10.1039/c4ra17050d

upstream raw materials:

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

methyl 3-O-benzyl-4-O-monochloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate)

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

methyl 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranosiduronate

Downstream raw materials:

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside