(R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

Base Information

Chemical Name:(R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester
CAS No.:910630-90-9
Molecular Formula:C₄₄H₅₉NO₈
Molecular Weight:729.954
Hs Code.:

Synonyms:(R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

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Chemical Property of (R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

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Technology Process of (R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

There total 5 articles about (R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl 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:

: 910630-82-9
(Z)-(7S,8R,9S)-7,8,9-Tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoic acid

: 13518-40-6,75898-43-0,104944-18-5
t-butyl D-valinate hydrochloride

: 910630-90-9
(R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h;
DOI:10.1021/ol061582d

Reference yield:

: 2771-55-3
2,3,4-tri-O-benzyl-D-galactopyranoside

: 910630-90-9
(R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / ethanol / 5 h / 20 °C

2: 2.05 mg / (1S)-(+)-10-camphorsulfonic acid / acetone / 3 h / 20 °C

3: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

4: 87 percent / LiHMDS / tetrahydrofuran / 2 h / 0 - 20 °C

5: BOP reagent; Huenig base / dimethylformamide / 4 h / 0 - 20 °C

With sodium tetrahydroborate; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 3: Dess-Martin oxidation / 4: Wittig reaction;
DOI:10.1021/ol061582d

Reference yield:

: 2771-56-4
2,3,4-Tri-O-benzyl-D-galactit

: 910630-90-9
(R)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2.05 mg / (1S)-(+)-10-camphorsulfonic acid / acetone / 3 h / 20 °C

2: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

3: 87 percent / LiHMDS / tetrahydrofuran / 2 h / 0 - 20 °C

4: BOP reagent; Huenig base / dimethylformamide / 4 h / 0 - 20 °C

With sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 2: Dess-Martin oxidation / 3: Wittig reaction;
DOI:10.1021/ol061582d