allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 628281-92-5
• Molecular Formula: C₅₂H₅₇N₃O₁₂
• Molecular Weight: 916.037

Synonyms:allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

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Safty Information:

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Technology Process of allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 13 articles about allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-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: 76.0%

4-methoxybenzyl N-phenyl-2,2,2-trifluoroacetimidate (1450734-54-9) + allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside (727380-38-3) → allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (628281-92-5)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In toluene; at 20 ℃; for 5h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.07.066

Reference yield:

allyl 2-azido-2-deoxy-α-D-glucopyranoside (152432-87-6) → allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (628281-92-5)

Guidance literature:

Multi-step reaction with 10 steps

1: (+/-)-camphorsulfonic acid / acetonitrile / 8 h

2: 99 percent / NaH / dimethylformamide / 0.58 h / 0 °C

3: 90 percent / NaBH₃CN; HCl; 4A MS / methyl orange / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

4: 4A MS; silver triflate / CH₂Cl₂ / 2.5 h / -40 °C

5: 10.9 g / MeONa / methanol

6: 89 percent / camphorsulfonic acid / acetonitrile / 1 h / 20 °C

7: 97 percent / NaH / dimethylformamide / 20 °C

8: 91 percent / triethylsilane; 4A MS; dichlorophenylborane / diethyl ether / -40 °C

9: oxalyl chloride; DMSO / CH₂Cl₂ / 0.75 h / -78 °C

10: 405 mg / KOH; I₂ / 1 h / 0 °C

With hydrogenchloride; triethylsilane; potassium hydroxide; oxalyl dichloride; camphor-10-sulfonic acid; phenylborondichloride; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200300254

Reference yield:

allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (628280-97-7) → allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (628281-92-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / NaH / dimethylformamide / 0.58 h / 0 °C

2: 90 percent / NaBH₃CN; HCl; 4A MS / methyl orange / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

3: 4A MS; silver triflate / CH₂Cl₂ / 2.5 h / -40 °C

4: 10.9 g / MeONa / methanol

5: 89 percent / camphorsulfonic acid / acetonitrile / 1 h / 20 °C

6: 97 percent / NaH / dimethylformamide / 20 °C

7: 91 percent / triethylsilane; 4A MS; dichlorophenylborane / diethyl ether / -40 °C

8: oxalyl chloride; DMSO / CH₂Cl₂ / 0.75 h / -78 °C

9: 405 mg / KOH; I₂ / 1 h / 0 °C

With hydrogenchloride; triethylsilane; potassium hydroxide; oxalyl dichloride; camphor-10-sulfonic acid; phenylborondichloride; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200300254

upstream raw materials:

methanol

methyl iodide

(2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

3-[(3-benzyloxycarbonylamino)propylthio]propyl (methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate)-(1-4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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