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

Base Information

• Chemical Name: 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
• CAS No.: 158356-07-1
• Molecular Formula: C₂₇H₃₅NO₈
• Molecular Weight: 501.577
• Mol file: 158356-07-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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:

p-Anisaldehyde dimethyl acetal (2186-92-7) → 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 (158356-07-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) p-TsOH*H₂O, 2.) NaBH₄, 3.) p-TsOH*H₂O

2: oxalyl chloride in DMSO, Et₃N

3: LDA / tetrahydrofuran / -78 °C

4: 71 percent / NaN₃, 15-crown-5 / hexamethylphosphoric acid triamide / 100 °C

5: 100 percent / NaBH₄ / ethanol

6: 100 percent / i-Pr₂EtN / CH₂Cl₂

7: H₂ / 10percent Pd/C / ethanol

8: pyridine

9: 86 percent / NaBH₃CN, TMSCl / acetonitrile

10: oxalyl chloride in DMSO, Et₃N

With pyridine; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; oxalyl dichloride; 15-crown-5; hydrogen; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.42.994

Reference yield:

2,2-dimethoxy-propane (77-76-9) → 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 (158356-07-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) p-TsOH*H₂O, 2.) NaBH₄, 3.) p-TsOH*H₂O

2: oxalyl chloride in DMSO, Et₃N

3: LDA / tetrahydrofuran / -78 °C

4: 71 percent / NaN₃, 15-crown-5 / hexamethylphosphoric acid triamide / 100 °C

5: 100 percent / NaBH₄ / ethanol

6: 100 percent / i-Pr₂EtN / CH₂Cl₂

7: H₂ / 10percent Pd/C / ethanol

8: pyridine

9: 86 percent / NaBH₃CN, TMSCl / acetonitrile

10: oxalyl chloride in DMSO, Et₃N

With pyridine; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; oxalyl dichloride; 15-crown-5; hydrogen; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.42.994

Reference yield:

1,3-O-p-methoxybenzylidene-4,6-O-isopropylidene-D-glucitol → 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 (158356-07-1)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; oxalyl dichloride; 15-crown-5; hydrogen; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetonitrile;

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

p-Anisaldehyde dimethyl acetal

2,2-dimethoxy-propane

Downstream raw materials:

myriocin

(S)-2-Benzoylamino-2-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-propionic acid methyl ester

Z-myriocin

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