(2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester
• CAS No.: 186831-59-4
• Molecular Formula: C₄₄H₅₆O₂₀
• Molecular Weight: 904.917

Synonyms:(2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Chemical Property of (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Chemical Property:

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Technology Process of (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

There total 14 articles about (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl 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: 70.0%

(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester (186831-58-3) + 5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide (186831-49-2) → (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester (186831-59-4)

Guidance literature:

With molecular sives 3 Angstroem; mercury(II) cyanide; In dichloromethane; for 3h;

DOI:10.1016/S0008-6215(97)10073-8

Reference yield:

benzyl bromide (100-39-0) → (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester (186831-59-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / Ag₂O / acetonitrile; dimethylformamide / Ambient temperature

2: 93 percent / CSA / CH₂Cl₂; methanol / 1 h / Ambient temperature

3: 1.) aq. NaHCO₃, KBr, TEMPO, NaOCl, 2.) 1M Me₃SiCl / 1.) CH₂Cl₂, 1 h, 0 deg C; 2.) CH₂Cl₂

4: 70 percent / Hg(CN)2, molecular sives 3 Angstroem / CH₂Cl₂ / 3 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; chloro-trimethyl-silane; molecular sives 3 Angstroem; camphor-10-sulfonic acid; mercury(II) cyanide; sodium hydrogencarbonate; potassium bromide; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0008-6215(97)10073-8

Reference yield:

1,2,3,4-tetra-O-acetyl-6-deoxy-α-L-talopyranose (143394-72-3) → (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester (186831-59-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 79.5 percent / Cl₂CHOCH₃ (DCMME), ZnCl₂ / CH₂Cl₂ / Ambient temperature

2: 73 percent / AgOTf, sym.-collidine / CH₂Cl₂ / 0.5 h / -40 °C

3: 71 percent / TfOH / Ambient temperature

4: TiBr₄ / CH₂Cl₂; acetic acid / 1 h / Ambient temperature

5: 70 percent / Hg(CN)2, molecular sives 3 Angstroem / CH₂Cl₂ / 3 h

With 2,4,6-trimethyl-pyridine; trifluorormethanesulfonic acid; Dichloromethyl methyl ether; molecular sives 3 Angstroem; silver trifluoromethanesulfonate; mercury(II) cyanide; titanium(IV) bromide; zinc(II) chloride; In dichloromethane; acetic acid;

DOI:10.1016/S0008-6215(97)10073-8

upstream raw materials:

(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

benzyl bromide

2,3,4-O-triacetyl-6-deoxy-α-L-talose

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