allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

Base Information

Chemical Name:allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside
CAS No.:132791-89-0
Molecular Formula:C₆₇H₁₀₆FNO₁₄
Molecular Weight:1168.58
Hs Code.:

allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

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Chemical Property of allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

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Technology Process of allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

There total 14 articles about allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-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: 29.0%

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

: 132791-91-4,132882-51-0
allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

: 132791-89-0,132881-14-2
allyl 6-O-benzyloxycarbonyl-2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

: (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-5-benzyloxycarbonyloxy-3-((2S,3R)-3-benzyloxycarbonyloxy-2-fluoro-tetradecanoylamino)-6-benzyloxycarbonyloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With dmap; In dichloromethane; at 3 ℃; for 1h;
DOI:10.1248/cpb.40.333

Reference yield: 12.0%

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

: 132791-91-4,132882-51-0
allyl 2-<(2R,3S)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

: 132791-89-0,132881-14-2
allyl 6-O-benzyloxycarbonyl-2-<(2R,3S)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

: (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-5-benzyloxycarbonyloxy-3-((2R,3S)-3-benzyloxycarbonyloxy-2-fluoro-tetradecanoylamino)-6-benzyloxycarbonyloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With dmap; In dichloromethane; at 3 ℃; for 1h;
DOI:10.1248/cpb.40.333

Reference yield:

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

: 132791-89-0,132881-14-2
allyl 6-O-benzyloxycarbonyl-2-<(2R,3S)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / DMAP, DCC / CH₂Cl₂ / 2 h / 25 °C

2: 77 percent / 90percent aq. AcOH / 1 h / 55 - 60 °C

3: 75 percent / DMAP / CH₂Cl₂ / 1 h / 3 °C

With dmap; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1248/cpb.40.333