4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate

Base Information

• Chemical Name: 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate
• CAS No.: 139623-11-3
• Molecular Formula: C₆₉H₉₆NO₁₁P
• Molecular Weight: 1146.5

Synonyms:4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate

Chemical Property of 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate

There total 17 articles about 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate 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: 63.0%

dibenzyl phosphochloridate (538-37-4) + 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-D-glucopyranose → 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate (139623-11-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

DOI:10.1016/0008-6215(91)89006-2

Reference yield:

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) → 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate (139623-11-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 76 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Ambient temperature

2: 36.9 g / pyridine / 2 h / 60 °C

3: NaH / tetrahydrofuran / 16 h / Heating

4: p-TsOH*H₂O / methanol / 0.75 h / Ambient temperature

5: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 15 - 20 °C

6: 53 percent / NaH / dimethylformamide / 3 h / Ambient temperature

7: 92 percent / EtOH, 1M NaOH / 1.5 h / Heating

8: 93 percent / N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.5 h / 20 °C

9: 80percent AcOH / 0.5 h / 60 °C

10: 99 percent / p-TsOH / dimethylformamide / 20 - 25 °C

11: 2) pyridin, I₂ / 1) 8H₁₂Ir(PMePh₂)2>PF₆ / 1) 2h, 20 deg C, 2) 20 min, 20 deg C

12: 63 percent / BuLi / hexane; tetrahydrofuran / 0.17 h / -78 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; ethanol; iodine; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; PF6; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)89006-2

Reference yield:

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose (667462-08-0) → 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate (139623-11-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 2percent HCl / 0.5 h / Heating

2: 28.7 percent / pyridinium p-toluenesulfonate / dimethylformamide / 3 h / Ambient temperature

3: 53 percent / NaH / dimethylformamide / 3 h / Ambient temperature

4: 92 percent / EtOH, 1M NaOH / 1.5 h / Heating

5: 93 percent / N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.5 h / 20 °C

6: 80percent AcOH / 0.5 h / 60 °C

7: 99 percent / p-TsOH / dimethylformamide / 20 - 25 °C

8: 2) pyridin, I₂ / 1) 8H₁₂Ir(PMePh₂)2>PF₆ / 1) 2h, 20 deg C, 2) 20 min, 20 deg C

9: 63 percent / BuLi / hexane; tetrahydrofuran / 0.17 h / -78 °C

With pyridine; hydrogenchloride; sodium hydroxide; n-butyllithium; ethanol; iodine; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; PF6; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)89006-2

upstream raw materials:

dibenzyl phosphochloridate

(R)-3-hydroxytetradecanoic acid

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose

D-(+)-glucosamine hydrochloride

Downstream raw materials:

2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-3-O-<(3R)-3-hydroxytetradecanyl>-α-D-glucopyranosyl dihydrogen phosphate

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