{(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

Base Information

• Chemical Name: {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester
• CAS No.: 189071-51-0
• Molecular Formula: C₂₃H₃₉NO₁₃
• Molecular Weight: 537.562

Synonyms:{(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

Chemical Property of {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester

There total 10 articles about {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic 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: 90.0%

{(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester (178272-07-6) → {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester (189071-51-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 8h; under 760 Torr; Ambient temperature;

DOI:10.1021/ja952265x

Reference yield:

3-Desoxy-D-lyxo-heptulosansaeure (29873-81-2) → {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester (189071-51-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / Dowex 50W-X₈ (H⁺) / 2 h / Heating

2: camphorsulfonic acid / dimethylformamide / 12 h / 60 °C

3: aq. LiOH / methanol / 2 h / Ambient temperature

4: 58 percent / HOBt, 4-methylmorpholine, EDC / dimethylformamide / 12 h / -20 - 25 °C

5: 53 percent / NaH, Bu₄NI / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 4 h

6: 90 percent / H₂ / 20percent Pd(OH)2/C / methanol / 8 h / 760 Torr / Ambient temperature

With 4-methyl-morpholine; lithium hydroxide; Dowex 50W-X₈ (H⁺); camphor-10-sulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja952265x

Reference yield:

(1R,2R)-trans-2-azidocyclohexanol (110716-78-4) → {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester (189071-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 4A molecular sieves, TfOH / CH₂Cl₂ / 1 h / -15 °C

2: 97 percent / water / benzene / 15 h / Heating

3: 58 percent / HOBt, 4-methylmorpholine, EDC / dimethylformamide / 12 h / -20 - 25 °C

4: 53 percent / NaH, Bu₄NI / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 4 h

5: 90 percent / H₂ / 20percent Pd(OH)2/C / methanol / 8 h / 760 Torr / Ambient temperature

With 4-methyl-morpholine; trifluorormethanesulfonic acid; 4 A molecular sieve; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja952265x

upstream raw materials:

{(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester

3-Desoxy-D-lyxo-heptulosansaeure

(1R,2R)-trans-2-azidocyclohexanol

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite

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