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

Base Information

Chemical Name:ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-α-D-gluco-heptofuranuronate
CAS No.:631918-73-5
Molecular Formula:C₃₀H₃₉NO₈
Molecular Weight:541.642
Hs Code.:

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

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

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

There total 1 articles about ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-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: 71.0%

: 105-36-2
ethyl bromoacetate

: 329361-73-1
(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-α-D-glucoheptofurannuronate

: 631918-73-5
ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-α-D-gluco-heptofuranuronate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 30h;
DOI:10.1016/S0968-0896(03)00231-1

Reference yield: 82.0%

: 631918-73-5
ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-α-D-gluco-heptofuranuronate

: 631918-75-7
1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-2-hydroxyethyl)amino-5,6-dideoxy-α-D-gluco-heptofuranose

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/S0968-0896(03)00231-1

Reference yield:

: 631918-73-5
ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-α-D-gluco-heptofuranuronate

: Acetic acid (2R,3R,4R)-2-{(R)-3-acetoxy-1-[(2-acetoxy-ethyl)-benzyloxycarbonyl-amino]-propyl}-4,5-dihydroxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / LAH / tetrahydrofuran / 2 h / 20 °C

2: 84 percent / pyridine / 4 h / 25 °C

3: 89 percent / hydrogen / Pd/C / methanol / 12 h / 20 °C / 4137.18 Torr

4: 88 percent / NaHCO₃ / ethanol; H₂O / 4 h / 20 °C

5: 94 percent / pyridine / 3 h / 20 °C

6: TFA; water / 3 h / 30 °C

With pyridine; lithium aluminium tetrahydride; water; hydrogen; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;
DOI:10.1016/S0968-0896(03)00231-1