N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide

Base Information

• Chemical Name: N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide
• CAS No.: 158356-13-9
• Molecular Formula: C₂₈H₄₁NO₆
• Molecular Weight: 487.637
• Mol file: 158356-13-9.mol

Synonyms:N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide

Chemical Property of N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide

There total 16 articles about N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide 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: 67.0%

(S)-2-Benzoylamino-2-{(4R,5R)-5-[(Z)-9-(2-hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-propionic acid methyl ester → N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide (158356-13-9)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 2h; Heating;

DOI:10.1016/0040-4020(95)00279-H

Reference yield: 17.0%

(S)-2-Benzoylamino-2-{(4R,5R)-5-[(E)-9-(2-hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-propionic acid methyl ester → N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide (158356-13-9) + N-benzoylanhydromyriocin (158356-12-8)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; water;

DOI:10.1248/cpb.42.994

Reference yield:

1,3-O-p-methoxybenzylidene-4,6-O-isopropylidene-D-glucitol → N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide (158356-13-9)

Guidance literature:

Multi-step reaction with 15 steps

1: oxalyl chloride in DMSO, Et₃N

2: LDA / tetrahydrofuran / -78 °C

3: 71 percent / NaN₃, 15-crown-5 / hexamethylphosphoric acid triamide / 100 °C

4: 100 percent / NaBH₄ / ethanol

5: 100 percent / i-Pr₂EtN / CH₂Cl₂

6: H₂ / 10percent Pd/C / ethanol

7: pyridine

8: 86 percent / NaBH₃CN, TMSCl / acetonitrile

9: oxalyl chloride in DMSO, Et₃N

10: NaClO₂, NH₂SO₃H / dioxane; H₂O

11: diethyl ether

12: DDQ / CH₂Cl₂; H₂O

13: oxalyl chloride in DMSO, Et₃N

14: 65 percent / n-BuLi / 2-methyl-propan-2-ol; tetrahydrofuran

15: 50 percent / p-TsOH*H₂O / ethanol; H₂O

With pyridine; sodium chlorite; sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; sodium azide; oxalyl dichloride; 15-crown-5; aminosulfonic acid; hydrogen; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.42.994

upstream raw materials:

N-((S)-1-Hydroxymethyl-1-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-ethyl)-benzamide

N-((S)-1-Formyl-1-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-ethyl)-benzamide

Downstream raw materials:

Z-myriocin