2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Base Information

• Chemical Name: 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside
• CAS No.: 890131-37-0
• Molecular Formula: C₄₄H₄₀Cl₅NO₁₆
• Molecular Weight: 1016.06

Synonyms:2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Chemical Property of 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Chemical Property:

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Technology Process of 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

There total 12 articles about 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-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: 89.0%

2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside (890131-36-9) → 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside (890131-37-0)

Guidance literature:

With pyridine; hydrazinium monoacetate; at 20 ℃; for 0.133333h;

DOI:10.1002/anie.200503551

Reference yield:

O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-1,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-D-galactopyranose → 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside (890131-37-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / n-Bu₄NBr; BF₃*Et₂O; TMSBr / 2,4,6-collidine / CH₂Cl₂ / 48 h / 20 °C

2: 90 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h

3: NaOMe / methanol

4: trifluoroacetic acid / 4 h

5: 83 percent / camphorsulfonic acid / dimethylformamide / 1.5 h

6: 92 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

7: 79 percent / AcOH / CH₂Cl₂; H₂O / 24 h / 20 °C

8: 95 percent / pyridine / 1 h / 0 °C

9: AcOH / 0.5 h / 100 °C

10: pyridine / CH₂Cl₂ / 1 h / 0 °C

11: 89 percent / hydrazine acetate; pyridine / 0.13 h / 20 °C

With pyridine; dmap; trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; hydrazinium monoacetate; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,4,6-trimethyl-pyridine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503551

Reference yield:

O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2-trichloromethyl-(4,6-di-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]2-oxazoline (890131-32-5) → 2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside (890131-37-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h

2: NaOMe / methanol

3: trifluoroacetic acid / 4 h

4: 83 percent / camphorsulfonic acid / dimethylformamide / 1.5 h

5: 92 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

6: 79 percent / AcOH / CH₂Cl₂; H₂O / 24 h / 20 °C

7: 95 percent / pyridine / 1 h / 0 °C

8: AcOH / 0.5 h / 100 °C

9: pyridine / CH₂Cl₂ / 1 h / 0 °C

10: 89 percent / hydrazine acetate; pyridine / 0.13 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; hydrazinium monoacetate; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503551

upstream raw materials:

2-naphthylmethyl O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2-trichloromethyl-(4,6-di-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]2-oxazoline

(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[(2S,4aR,6R,7R,8R,8aR)-6-(naphthalen-2-ylmethoxy)-2-phenyl-7-(2,2,2-trichloro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

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