(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester
CAS No.:112166-33-3
Molecular Formula:C₅₈H₉₆NO₁₃P
Molecular Weight:1046.37
Hs Code.:

(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

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Chemical Property of (R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

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Technology Process of (R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

There total 9 articles about (R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester 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:

: 112166-27-5
benzyl 3-O-<(3R)-3-(benzyloxymethoxy)tetradecanoyl>-2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-dodecanoyloxytetradecanamido>-β-D-glucopyranoside

: 112166-33-3,112166-43-5
(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol;
DOI:10.1016/0008-6215(87)80220-3

Reference yield:

: 112-16-3
n-dodecanoyl chloride

: 112166-33-3,112166-43-5
(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 95.3 percent / DMAP / CH₂Cl₂; pyridine / Ambient temperature

2: zinc dust, acetic acid / 50 °C

3: 90 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

4: 98.2 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

5: 94.5 percent / 95percent acetic acid

6: 91 percent / pyridine / 6 h / 90 °C

7: 1.) 4-(dimethylamino)pyridine / 1.) CH₂Cl₂, pyridine; 2.) detritylation

8: hydrogen / 10percent palladium-carbon / methanol

With dmap; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; palladium on activated charcoal; In pyridine; methanol; dichloromethane;
DOI:10.1016/0008-6215(87)80220-3

Reference yield:

: 107856-74-6
C₂₆H₅₀O₄

: 112166-33-3,112166-43-5
(R)-3-Hydroxy-tetradecanoic acid (2R,3S,4R,5R)-3-(diphenoxy-phosphoryloxy)-5-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxy-2-hydroxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

2: 98.2 percent / 3-(3-dimethylamino)propyl-1-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

3: 94.5 percent / 95percent acetic acid

4: 91 percent / pyridine / 6 h / 90 °C

5: 1.) 4-(dimethylamino)pyridine / 1.) CH₂Cl₂, pyridine; 2.) detritylation

6: hydrogen / 10percent palladium-carbon / methanol

With dmap; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In pyridine; methanol; dichloromethane;
DOI:10.1016/0008-6215(87)80220-3