(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 701976-82-1
• Molecular Formula: C₃₈H₄₅N₃O₁₂
• Molecular Weight: 735.788

Synonyms:(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 5 articles about (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 71.0%

allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (701976-77-4) → (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (701976-82-1)

Guidance literature:

allyl (methyl 3-O-benzyl-2,4-O-(4-methoxybenzylidene)-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside; With triethylsilane; 4 A molecular sieve; In diethyl ether; at 20 ℃; 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) → (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (701976-82-1)

Guidance literature:

Multi-step reaction with 6 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: camphorsulfonic acid / CH₂Cl₂

5.2: 62 percent / methanolysis

6.1: triethylsilane; 4 Angstroem molecular sieves / diethyl ether / 0.5 h / 20 °C

6.2: 71 percent / dichlorophenylborane / diethyl ether / -78 - -40 °C

With methanol; triethylsilane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; potassium carbonate; mercury dichloride; mercury(II) oxide; In diethyl ether; dichloromethane; water; acetone;

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) → (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (701976-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / K₂CO₃; MeOH

2.1: camphorsulfonic acid / CH₂Cl₂

2.2: 62 percent / methanolysis

3.1: triethylsilane; 4 Angstroem molecular sieves / diethyl ether / 0.5 h / 20 °C

3.2: 71 percent / dichlorophenylborane / diethyl ether / -78 - -40 °C

With methanol; triethylsilane; 4 A molecular sieve; camphor-10-sulfonic acid; potassium carbonate; In diethyl ether; dichloromethane;

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-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

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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