1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol

Base Information

• Chemical Name: 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol
• CAS No.: 117300-19-3
• Molecular Formula: C₃₃H₄₂O₆
• Molecular Weight: 534.693

Synonyms:1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol

Chemical Property of 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol

There total 10 articles about 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol 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: 40.0%

(2S,3R,4R)-3-Benzyloxy-2-((1S,2S)-1,2-bis-benzyloxy-3-methoxymethoxy-2-methyl-propyl)-4-methoxymethoxy-hexan-1-ol (117325-11-8) → 1,4-anhydro-3-O-benzyl-2-C-(D-threo-1'-benzyloxy-2'-methoxymethoxybutyl)-2-deoxy-5-O-methoxymethyl-4-C-methyl-L-xylitol (117300-20-6) + 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol (117300-19-3)

Guidance literature:

With 2,4-dimethylaminopyridine; methanesulfonyl chloride; triethylamine; In dichloromethane; for 0.0833333h;

DOI:10.1016/0008-6215(88)85084-5

Reference yield:

(2S,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-iodomethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol → 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol (117300-19-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 4-dimethylaminopyridine / ethyl acetate / Ambient temperature

2: 95 percent / Zn, NH₄Cl / aq. ethanol / 0.5 h / Heating

3: H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature

4: pyridinium chlorochromate, anhydrous sodium acetate, florisil / CH₂Cl₂

5: 81 percent / CH₂Cl₂ / 16 h

6: ethyl di-isopropylamine / CH₂Cl₂

7: 20 percent / N-methylpiperazine, LiAlH₄ / tetrahydrofuran / 3.5 h / Heating

8: 21 percent / methanesulfonyl chloride, triethylamine, 2,4-dimethylaminopyridine / CH₂Cl₂ / 0.08 h / 0 °C

With 1-methyl-piperazine; dmap; florisil; lithium aluminium tetrahydride; 2,4-dimethylaminopyridine; hydrogen; sodium acetate; ammonium chloride; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/0008-6215(88)85084-5

Reference yield:

3-O-benzyl-2-deoxy-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-α-D-glucopyranoside (110046-71-4) → 1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol (117300-19-3)

Guidance literature:

Multi-step reaction with 9 steps

1: triphenylphosphine, iodine, imidazole / benzene / 0.5 h / Ambient temperature

2: 4-dimethylaminopyridine / ethyl acetate / Ambient temperature

3: 95 percent / Zn, NH₄Cl / aq. ethanol / 0.5 h / Heating

4: H₂ / 10 percent Pd/C / ethyl acetate / 2 h / Ambient temperature

5: pyridinium chlorochromate, anhydrous sodium acetate, florisil / CH₂Cl₂

6: 81 percent / CH₂Cl₂ / 16 h

7: ethyl di-isopropylamine / CH₂Cl₂

8: 20 percent / N-methylpiperazine, LiAlH₄ / tetrahydrofuran / 3.5 h / Heating

9: 21 percent / methanesulfonyl chloride, triethylamine, 2,4-dimethylaminopyridine / CH₂Cl₂ / 0.08 h / 0 °C

With 1-methyl-piperazine; 1H-imidazole; dmap; florisil; lithium aluminium tetrahydride; 2,4-dimethylaminopyridine; hydrogen; iodine; sodium acetate; ammonium chloride; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/0008-6215(88)85084-5

upstream raw materials:

(2S,3R,4R)-3-Benzyloxy-2-((1S,2S)-1,2-bis-benzyloxy-3-methoxymethoxy-2-methyl-propyl)-4-methoxymethoxy-hexan-1-ol

3,4-di-O-benzyl-2-C-(D-threo-1'-benzyloxy-2'-methoxymethoxybutyl)-2-deoxy-5-O-methoxymethyl-4-C-methyl-L-xylose

(2S,3R,4R)-3-Benzyloxy-2-((1S,2S)-1,2-bis-benzyloxy-3-hydroxy-2-methyl-propyl)-4-hydroxy-hexanoic acid dimethylamide

3-O-benzyl-2-deoxy-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-α-D-glucopyranoside

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