methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate

Base Information

• Chemical Name: methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate
• CAS No.: 130257-53-3
• Molecular Formula: C₄₆H₅₅N₃O₁₃
• Molecular Weight: 857.955

Synonyms:

Chemical Property of methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate

There total 14 articles about methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate 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:

triacetyl-D-galactal (4098-06-0) → methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate (130257-53-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / sodium, methanol

2: 11 percent / imidazole / dimethylformamide / 0.67 h / 0 °C

3: sodium hydride / tetrahydrofuran; dimethylformamide / 0.75 h / 0 °C

4: methanol / 4 h / 40 °C

5: 96 percent / sodium hydride / dimethylformamide / 1 h

6: 69 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2 h, 2) 1,4-dioxane, 1 h, 80 deg C

7: 81 percent / oxalyl bromide / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / 0 °C

8: 1) silver silicate, acetivated powdered 4 Angstroem molecular sieves, 2) Bu₄NF / 1) 1,2-dichloroethane, -20 deg C, 1 h, 2) THF, 1 h, 0 deg C

9: pyridinium dichromate / dimethylformamide / 20 h

10: 1,2-dichloro-ethane; diethyl ether

With 1H-imidazole; methanol; dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; Oxalyl bromide; silver silicate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium; sodium hydride; sodium nitrite; In tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84259-W

Reference yield:

benzyl bromide (100-39-0) → methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate (130257-53-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / sodium hydride / dimethylformamide / 1 h

2: 69 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2 h, 2) 1,4-dioxane, 1 h, 80 deg C

3: 81 percent / oxalyl bromide / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / 0 °C

4: 1) silver silicate, acetivated powdered 4 Angstroem molecular sieves, 2) Bu₄NF / 1) 1,2-dichloroethane, -20 deg C, 1 h, 2) THF, 1 h, 0 deg C

5: pyridinium dichromate / dimethylformamide / 20 h

6: 1,2-dichloro-ethane; diethyl ether

With dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; Oxalyl bromide; silver silicate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; sodium nitrite; In diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84259-W

Reference yield:

4-O-(2-methoxyethoxymethyl)-D-galactal (130257-30-6) → methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate (130257-53-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / sodium hydride / dimethylformamide / 1 h

2: 69 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2 h, 2) 1,4-dioxane, 1 h, 80 deg C

3: 81 percent / oxalyl bromide / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / 0 °C

4: 1) silver silicate, acetivated powdered 4 Angstroem molecular sieves, 2) Bu₄NF / 1) 1,2-dichloroethane, -20 deg C, 1 h, 2) THF, 1 h, 0 deg C

5: pyridinium dichromate / dimethylformamide / 20 h

6: 1,2-dichloro-ethane; diethyl ether

With dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; Oxalyl bromide; silver silicate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; sodium nitrite; In diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84259-W

upstream raw materials:

diazomethane

benzyl bromide

4-O-(2-methoxyethoxymethyl)-D-galactal

3,6-di-O-tert-butyldimethylsilyl-D-(-)-galactal

Downstream raw materials:

methyl 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid

methyl uronate

(2S,3S,4S,5R)-6-Acetoxy-3-((2S,3R,4R,5R,6R)-5-acetoxy-3-acetylamino-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt

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