(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

Base Information

Chemical Name:(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
CAS No.:920958-53-8
Molecular Formula:C₄₄H₅₅NO₁₂
Molecular Weight:789.92
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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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-(4-oxo-pentanoyloxy)-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-(4-oxo-pentanoyloxy)-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: 61.0%

: 920958-49-2
benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester

: 615543-18-5
methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate

: 920958-53-8
(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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - -10 ℃; for 0.5h;
DOI:10.1002/chem.200601103

Reference yield:

: 87905-98-4
5-<(benzyloxycarbonyl)amino>pentanol

: 920958-53-8
(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

Guidance literature:: Multi-step reaction with 4 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

With trimethylsilyl trifluoromethanesulfonate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200601103

Reference yield:

: 945224-35-1
2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

: 920958-53-8
(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

Guidance literature:: Multi-step reaction with 8 steps

1.1: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0.08 h

2.1: 94 percent / sulfur trioxide pyridine complex; DIPEA; dimethyl sulfoxide / CH₂Cl₂ / 0.25 h / 0 °C

3.1: MgBr₂*OEt₂ / CH₂Cl₂ / 20 °C

3.2: 73 percent / hydrazine acetate / CH₂Cl₂; methanol / 12 h / 20 °C

4.1: acetyl chloride / toluene / 0 - 20 °C

4.2: 70 percent / water / toluene / 0 - 20 °C

5.1: 4-dimethylaminopyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 2.5 h / 0 °C

6.1: bis(trifluoroacetoxy)iodobenzene; water; NaHCO₃ / acetonitrile / 0.5 h / 20 °C

6.2: trifluoroacetic acid / H₂O / 0.5 h / 50 °C

7.1: 461 mg / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

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

With triethylsilane; dmap; water; sulfur trioxide pyridine complex; sodium hydrogencarbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; magnesium bromide; diisopropyl-carbodiimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; acetonitrile; 2.1: Parikh-Doering oxidation / 4.1: Pinner reaction;
DOI:10.1002/chem.200700141