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

Base Information

Chemical Name: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
CAS No.:158356-06-0
Molecular Formula:C₂₇H₃₇NO₈
Molecular Weight:503.593
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 86.0%

: 158356-05-9
N-[(4R,5R,2'R,4'R)-5-Methoxymethoxymethyl-2'-(4-methoxy-phenyl)-2,2-dimethyl-[4,4']bi[[1,3]dioxanyl]-5-yl]-benzamide

: 158356-06-0
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

Guidance literature:: With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; at 25 ℃; for 3h;
DOI:10.1016/0040-4020(95)00279-H

Reference yield: 86.0%

: N-[(4S,5R,2'R,4'R)-5-Methoxymethoxymethyl-2'-(4-methoxy-phenyl)-2,2-dimethyl-[4,4']bi[[1,3]dioxanyl]-5-yl]-benzamide

: 158356-06-0
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

Guidance literature:: With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile;
DOI:10.1248/cpb.42.994

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 158356-06-0
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

Guidance literature:: Multi-step reaction with 9 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

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