ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate

Base Information

• Chemical Name: ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate
• CAS No.: 329361-74-2
• Molecular Formula: C₃₄H₃₉NO₈
• Molecular Weight: 589.686
• Mol file: 329361-74-2.mol

Synonyms:ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate

Chemical Property of ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate

There total 1 articles about ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate 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: 97.0%

benzyl chloroformate (501-53-1,94274-21-2) + (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-α-D-glucoheptofurannuronate (329361-73-1) → ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate (329361-74-2)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; at 30 ℃; for 3h;

DOI:10.1021/jo0010476

Reference yield: 96.0%

ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate (329361-74-2) → 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronic acid (329361-75-3)

Guidance literature:

With lithium hydroxide; In methanol; water; at 0 - 25 ℃;

DOI:10.1021/jo0010476

Reference yield:

ethyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate (329361-74-2) → 5,6,7,8-tetradeoxy-5,8-(N-benzoxycarbonylimino)-1,2-O-isopropylidene-α-D-gluco-oct-1,4-furanose

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / LiOH*H₂O / methanol; H₂O / 0 - 25 °C

2.1: Et₃N; ethylchloroformate / tetrahydrofuran / 0.5 h / 0 °C

2.2: 62 percent / diethyl ether / 1.5 h / 0 - 25 °C

3.1: 83 percent / PhCOOAg; Et₃N / 1.5 h / 25 °C

4.1: H₂ / 10percent Pd/C / methanol / 12 h / 4137.29 Torr

4.2: 80 percent / CH₃COONa / methanol / 6 h / Heating

5.1: LiAlH₄ / tetrahydrofuran / 18 h / Heating

6.1: NaHCO₃ / ethanol; H₂O / 2 h / 25 °C

With lithium hydroxide; lithium aluminium tetrahydride; hydrogen; silver benzoate; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1021/jo0010476

upstream raw materials:

benzyl chloroformate

(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-α-D-glucoheptofurannuronate

Downstream raw materials:

3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronic acid

1-deoxy-castanospermine

5,6,8-trideoxy-1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-8-diazo-α-D-gluco-octo-1,4-furan-7-ulose

methyl 3-O-benzyl-5-(N-benzyl-N-benzoxycarbonylamino)-5,6,7-trideoxy-1,2-O-isopropylidene-α-D-gluco-octo-1,4-furanuronate