(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate

Base Information

• Chemical Name: (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate
• CAS No.: 329361-79-7
• Molecular Formula: C₂₆H₃₃NO₆
• Molecular Weight: 455.551
• Mol file: 329361-79-7.mol

Synonyms:(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate

Chemical Property of (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate

There total 5 articles about (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate 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%

benzylamine (100-46-9) + (1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (404353-42-0) → (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-α-D-glucoheptofurannuronate (329361-73-1) + (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate (329361-79-7)

Guidance literature:

In ethanol;

DOI:10.1081/CAR-120016857

Reference yield: 85.0%

benzylamine (100-46-9) + (1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (404353-42-0) → (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate (329361-79-7)

Guidance literature:

In tetrahydrofuran; at -40 ℃; for 2h;

DOI:10.1021/jo0010476

Reference yield: 31.0%

C32H47NO7Si → (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-α-D-glucoheptofurannuronate (329361-73-1) + (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate (329361-79-7)

Guidance literature:

With copper diacetate; zinc; In water; acetic acid; at 70 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00981-9

upstream raw materials:

ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

benzylamine

(1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

3-O-benzyl-5,6-dideoxy-5-(N-benzyl)amino-1,2-O-isopropylidene-β-L-ido-hepto-1,4-furanose

ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptofuranuronate

ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate

(2S,3R,4R,5S)-1,2-Bis-(2-hydroxy-ethyl)-piperidine-3,4,5-triol