(2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

Base Information

Chemical Name:(2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane
CAS No.:160195-65-3
Molecular Formula:C₆₈H₁₀₃NO₆
Molecular Weight:1030.57
Hs Code.:

Synonyms:(2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

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Chemical Property of (2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

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Technology Process of (2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

There total 17 articles about (2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane 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: 95.0%

: 132842-23-0
(2R)-benzoyloxydocosanoic acid

: 160195-63-1
(2S,3S,4R)-2-amino-1,3,4-tribenzyloxy-16-methylheptadecane

: 160195-65-3
(2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1039/P19940002849

Reference yield:

: 160195-49-3
(2S,3R)-15-Methyl-hexadecane-1,2,3-triol

: 160195-65-3
(2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

Guidance literature:: Multi-step reaction with 17 steps

1: 66 percent / pyridine / 5 h / 0 °C

2: 97 percent / PPTS / benzene / 0.5 h / Heating

3: 100 percent / LiOH*H₂O / methanol / 3 h / 50 °C

4: 97 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 2 h

5: 2.) TBAF / 1.) THF, room temperature, 2 h, 2.) 30 min

6: 99 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 30 min

7: 96 percent / cerium(III) chloride, NaBH₄ / methanol / 0.17 h / Ambient temperature

8: NaH / dimethylformamide / 2 h / Ambient temperature

9: 1.) MeI, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) MeCN, 50 deg C, 48 h, 2.) MeOH, room temperature, 30 min, 3.) MeCN, H₂O, room temeperature, 30 min

10: 61 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

11: 96 percent / PTSA / methanol / 3 h / Ambient temperature

12: 90 percent / NaH, TBAI / dimethylformamide / 1.) 50 deg C, 1 h, 2.) room temperature, 5 h

13: 84 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

14: 100 percent / DMAP / pyridine / 3 h / Ambient temperature

15: 80 percent / LiN₃ / dimethylformamide / 48 h / 90 - 100 °C

16: 71 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

17: 95 percent / EDC*HCl / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; lithium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; copper dichloride; methyl iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19940002849

Reference yield:

: 160195-54-0
(2S,3R)-2,3-isopropylidenedioxy-15-methylhexadecan-1-ol

: 160195-65-3
(2S,3S,4R)-2-<(2'R)-benzoyloxydocosanoylamino>-1,3,4-tribenzyloxy-16-methylheptadecane

Guidance literature:: Multi-step reaction with 14 steps

1: 97 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 2 h

2: 2.) TBAF / 1.) THF, room temperature, 2 h, 2.) 30 min

3: 99 percent / oxalyl dichloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -50 deg C, 30 min

4: 96 percent / cerium(III) chloride, NaBH₄ / methanol / 0.17 h / Ambient temperature

5: NaH / dimethylformamide / 2 h / Ambient temperature

6: 1.) MeI, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) MeCN, 50 deg C, 48 h, 2.) MeOH, room temperature, 30 min, 3.) MeCN, H₂O, room temeperature, 30 min

7: 61 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

8: 96 percent / PTSA / methanol / 3 h / Ambient temperature

9: 90 percent / NaH, TBAI / dimethylformamide / 1.) 50 deg C, 1 h, 2.) room temperature, 5 h

10: 84 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

11: 100 percent / DMAP / pyridine / 3 h / Ambient temperature

12: 80 percent / LiN₃ / dimethylformamide / 48 h / 90 - 100 °C

13: 71 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

14: 95 percent / EDC*HCl / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; lithium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(II) oxide; copper dichloride; methyl iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/P19940002849