allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 701976-84-3
• Molecular Formula: C₄₀H₄₇N₃O₁₃
• Molecular Weight: 777.825

Synonyms:allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 6 articles about allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-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: 84.0%

allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (701976-78-5) → allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (701976-84-3)

Guidance literature:

allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside; With triethylsilane; 4 A molecular sieve; In diethyl ether; at 0 ℃; for 0.5h;

With phenylborondichloride; In diethyl ether; at -78 - -40 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.03.046

Reference yield:

methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate (87327-03-5) → allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (701976-84-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / HgO; HgCl₂ / acetone; H₂O

2.1: 86 percent / K₂CO₃ / CH₂Cl₂

3.1: 92 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 100 percent / K₂CO₃; MeOH

5.1: 85 percent / PPh₃; DIAD / tetrahydrofuran

6.1: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 0.5 h / Heating

7.1: triethylsilane; 4 Angstroem molecular sieves / diethyl ether / 0.5 h / 0 °C

7.2: 84 percent / dichlorophenylborane / diethyl ether / -78 - -40 °C

With methanol; triethylsilane; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; 4 A molecular sieve; camphor-10-sulfonic acid; potassium carbonate; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; 5.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2004.03.046

Reference yield:

allyl (methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (628280-99-9) → allyl (methyl 3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (701976-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / K₂CO₃; MeOH

2.1: 85 percent / PPh₃; DIAD / tetrahydrofuran

3.1: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 0.5 h / Heating

4.1: triethylsilane; 4 Angstroem molecular sieves / diethyl ether / 0.5 h / 0 °C

4.2: 84 percent / dichlorophenylborane / diethyl ether / -78 - -40 °C

With methanol; triethylsilane; di-isopropyl azodicarboxylate; 4 A molecular sieve; camphor-10-sulfonic acid; potassium carbonate; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2004.03.046

upstream raw materials:

allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate

allyl (methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-6-allyloxy-5-azido-4-benzyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-3,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

allyl [methyl 2-O-acetyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

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