(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

Base Information

Chemical Name:(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol
CAS No.:862718-92-1
Molecular Formula:C₇₁H₁₀₇NO₈
Molecular Weight:1102.63
Hs Code.:

Synonyms:(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

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Chemical Property of (3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

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Technology Process of (3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

There total 13 articles about (3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol 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: 48.0%

: (S)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propylamine

: 557-59-5
n-tetracosanoic acid

: 862718-92-1
(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/j.bmc.2012.03.025

Reference yield:

: 862718-88-5
(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

: 862718-92-1
(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / TsNHNH₂; aq. NaOAc / 1,2-dimethoxy-ethane / Heating

2: 94 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3: NaN₃ / dimethylformamide / 90 °C

4: H₂ / Pd/CaCO₃ / ethanol / 20 °C

5: EDCI*HCl; HOAt; Et₃N / dimethylformamide; CH₂Cl₂ / 20 °C

With pyridine; sodium azide; 1-hydroxy-7-aza-benzotriazole; hydrogen; sodium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; toluene-4-sulfonic acid hydrazide; Lindlar's catalyst; In 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.05.069

Reference yield:

: (2R,3S,4R,5S,6R)-2-[(S)-3-Azido-3-((4S,5R)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-propyl]-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

: 862718-92-1
(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / Pd/CaCO₃ / ethanol / 20 °C

2: EDCI*HCl; HOAt; Et₃N / dimethylformamide; CH₂Cl₂ / 20 °C

With 1-hydroxy-7-aza-benzotriazole; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; Lindlar's catalyst; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.05.069