(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 920958-09-4
• Molecular Formula: C₃₉H₄₉NO₁₀
• Molecular Weight: 691.819

Synonyms:(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 22 articles about (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-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: 96.0%

(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (920958-53-8) → (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (920958-09-4)

Guidance literature:

With pyridine; hydrazine hydrate; acetic acid; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1002/chem.200700141

Reference yield:

5-<(benzyloxycarbonyl)amino>pentanol (87905-98-4) → (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (920958-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / pyridine / 20 °C

2: 94 percent / NaH; TBAI / dimethylformamide / 1.5 h / 20 °C

3: 92 percent / TFA; H₂O / CH₂Cl₂ / 3 h / 20 °C

4: 61 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -20 - -10 °C

5: 91 percent / pyridine; acetic acid; hydrazine monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; hydrazine hydrate; acetic acid; trifluoroacetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200601103

Reference yield:

methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate (615543-18-5) → (2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (920958-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TMSOTf / CH₂Cl₂ / 0.5 h / -20 - -10 °C

2: 96 percent / pyridine; acetic acid; hydrazine monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; hydrazine hydrate; acetic acid; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1002/chem.200700141

upstream raw materials:

(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-D-xylose di(ethylthio)acetal

C₂₆H₃₈O₇S₂

Downstream raw materials:

C₆₁H₇₂O₁₅N₄

C₅₅H₆₄O₂₀N₂S₂

C₅₃H₆₂O₁₉N₂S₂

C₅₃H₆₀O₁₉N₄S₂

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