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

Base Information

• Chemical Name: methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside
• CAS No.: 109914-78-5
• Molecular Formula: C₄₃H₄₉NO₁₂
• Molecular Weight: 771.862

Synonyms:

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

There total 15 articles about methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-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,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetoxy-5-acetylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid → methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside (109914-78-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 5h; Yield given;

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

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-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside (109914-78-5)

Guidance literature:

Multi-step reaction with 9 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

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; 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-(2,3,4-tri-O-benzyl-α-L-idopyranosyluronic acid)-β-D-galactopyranoside (109914-78-5)

Guidance literature:

Multi-step reaction with 10 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

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; ethanol; water; acetone;

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

upstream raw materials:

(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

methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

benzyl bromide

Downstream raw materials:

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

methyl 2-acetamido-2-deoxy-3-O-(α-L-idopyranosyluronic acid)-4-O-sulfo-β-D-galactopyranoside, disodium salt

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

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