methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside
• CAS No.: 109914-79-6
• Molecular Formula: C₄₄H₅₁NO₁₂
• Molecular Weight: 785.888
• Mol file: 109914-79-6.mol

Synonyms:

Chemical Property of methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside

There total 16 articles about methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-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:

(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4-diol (87376-50-9) → methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside (109914-79-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / toluene-p-sulfonic acid monohydrate / 5 h / Ambient temperature

2: 97 percent / pyridine

3: 1) sodium hydride 2) 90 percent aq. trifluoroacetic acid / 1) N,N-dimethylformamid, stirred for 1 h 2) room temp., 10 min.

4: toluene-p-sulfonic acid monohydrate 2) 80 percent aq. acetic acid / 1) toluene, room temp., 1 h 2) room temp., 10 min.

6: 4 percent nickel dichloride hexahydrate, 2 percent boric acid, sodium borohydride / ethanol; tetrahydrofuran

7: M sodium hydroxyde / methanol / 0.25 h

8: chromium trioxide, sulfuric acid / acetone; H₂O / 0.25 h / 0 °C

9: 3 M sodium hydroxide / methanol; tetrahydrofuran / 5 h / 0 °C

10: diethyl ether / 0.33 h / Ambient temperature

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; boric acid; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; nickel dichloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone;

DOI:10.1016/S0008-6215(00)90218-0

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate (68733-05-1) → methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside (109914-79-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 60 percent / M sodium methoxyde / 1 h / Ambient temperature

2: 61 percent / toluene-p-sulfonic acid monohydrate / 5 h / Ambient temperature

3: 97 percent / pyridine

4: 1) sodium hydride 2) 90 percent aq. trifluoroacetic acid / 1) N,N-dimethylformamid, stirred for 1 h 2) room temp., 10 min.

5: toluene-p-sulfonic acid monohydrate 2) 80 percent aq. acetic acid / 1) toluene, room temp., 1 h 2) room temp., 10 min.

7: 4 percent nickel dichloride hexahydrate, 2 percent boric acid, sodium borohydride / ethanol; tetrahydrofuran

8: M sodium hydroxyde / methanol / 0.25 h

9: chromium trioxide, sulfuric acid / acetone; H₂O / 0.25 h / 0 °C

10: 3 M sodium hydroxide / methanol; tetrahydrofuran / 5 h / 0 °C

11: diethyl ether / 0.33 h / Ambient temperature

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; sodium methylate; boric acid; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; nickel dichloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone;

DOI:10.1016/S0008-6215(00)90218-0

Reference yield:

methyl 2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-57-0) → methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-benzyl-α-L-idopyranuronate)-β-D-galactopyranoside (109914-79-6)

Guidance literature:

Multi-step reaction with 7 steps

1: toluene-p-sulfonic acid monohydrate 2) 80 percent aq. acetic acid / 1) toluene, room temp., 1 h 2) room temp., 10 min.

3: 4 percent nickel dichloride hexahydrate, 2 percent boric acid, sodium borohydride / ethanol; tetrahydrofuran

4: M sodium hydroxyde / methanol / 0.25 h

5: chromium trioxide, sulfuric acid / acetone; H₂O / 0.25 h / 0 °C

6: 3 M sodium hydroxide / methanol; tetrahydrofuran / 5 h / 0 °C

7: diethyl ether / 0.33 h / Ambient temperature

With chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; boric acid; toluene-4-sulfonic acid; acetic acid; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone;

DOI:10.1016/S0008-6215(00)90218-0

upstream raw materials:

diazomethane

methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside

(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4-diol

methyl 2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside