allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

Base Information

Chemical Name:allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside
CAS No.:138527-88-5
Molecular Formula:C₆₆H₁₀₇NO₁₂
Molecular Weight:1106.58
Hs Code.:

Synonyms:allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

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Chemical Property of allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

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Technology Process of allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

There total 7 articles about allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside 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: 65.0%

: 138527-87-4
allyl 2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

: 501-53-1,94274-21-2
benzyl chloroformate

: 138527-88-5
allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1016/0008-6215(91)89008-4

Reference yield:

: 87357-76-4
(R)-3-(dodecanoyloxy)tetradecanoic acid

: 138527-88-5
allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / N,N-dicyclohexylcarbodiimide, DMPA / tetrahydrofuran / 4 h

2: 69 percent / 90percent aq. AcOH / 0.83 h / 60 °C

3: 65 percent / DMAP / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0008-6215(91)89008-4

Reference yield:

: 138527-55-6
allyl 2-amino-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

: 138527-88-5
allyl 6-O-(benzyloxycarbonyl)-2-<(3S)-3-(benzyloxy)tetradecanamido>-2-deoxy-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 35 percent / N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 1 h / 25 °C

2: 73 percent / N,N-dicyclohexylcarbodiimide, DMPA / tetrahydrofuran / 4 h

3: 69 percent / 90percent aq. AcOH / 0.83 h / 60 °C

4: 65 percent / DMAP / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0008-6215(91)89008-4