methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside
• CAS No.: 130257-56-6
• Molecular Formula: C₄₃H₄₉N₃O₁₁
• Molecular Weight: 783.876

Synonyms:methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside

Chemical Property of methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside

There total 14 articles about methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-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:

Acetic acid (2R,3R,4R,5R,6S)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester → methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside (130257-56-6) + Acetic acid (2R,3S,4R,5R,6R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.333333h; Yield given. Yields of byproduct given;

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

Reference yield:

triacetyl-D-galactal (4098-06-0) → methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside (130257-56-6)

Guidance literature:

Multi-step reaction with 11 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: trifluoroacetic acid / H₂O / 0.25 h / Ambient temperature

8: pyridine

9: 81 percent / 1,8-diazobicyclo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2.5 h / Ambient temperature

10: activated powdered 4 Angstroem molecular sieves, BF₃*OEt₂ / toluene; CH₂Cl₂ / 3 h / -20 °C

11: Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

With pyridine; 1H-imidazole; methanol; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; sodium nitrite; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

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

Reference yield:

benzyl bromide (100-39-0) → methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside (130257-56-6)

Guidance literature:

Multi-step reaction with 7 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: trifluoroacetic acid / H₂O / 0.25 h / Ambient temperature

4: pyridine

5: 81 percent / 1,8-diazobicyclo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2.5 h / Ambient temperature

6: activated powdered 4 Angstroem molecular sieves, BF₃*OEt₂ / toluene; CH₂Cl₂ / 3 h / -20 °C

7: Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

With pyridine; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; sodium nitrite; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

benzyl bromide

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

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

Downstream raw materials:

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

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

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

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