allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

Base Information

Chemical Name:allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside
CAS No.:132791-96-9
Molecular Formula:C₇₁H₁₀₀NO₁₂P
Molecular Weight:1190.55
Hs Code.:

allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

Synonyms:allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

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Chemical Property of allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

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Technology Process of allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

There total 17 articles about allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-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: 99.0%

: 132791-95-8
allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranoside

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 132791-96-9
allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

Guidance literature:: With 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; In dichloromethane; at 25 ℃; for 15h;
DOI:10.1016/0008-6215(91)89006-2

Reference yield:

: 28715-21-1,3422-31-9
(R)-3-hydroxytetradecanoic acid

: 132791-96-9
allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 11 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: 38 percent / Me₂NCONMe₂ / CH₂Cl₂ / 15 h / 25 °C

11: 99 percent / DMPA / CH₂Cl₂ / 15 h / 25 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; ethanol; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; tetramethylurea; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)89006-2

Reference yield:

: 667462-08-0
2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose

: 132791-96-9
allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 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: 38 percent / Me₂NCONMe₂ / CH₂Cl₂ / 15 h / 25 °C

8: 99 percent / DMPA / CH₂Cl₂ / 15 h / 25 °C

With hydrogenchloride; sodium hydroxide; ethanol; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; tetramethylurea; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(91)89006-2