(S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

Base Information

Chemical Name:(S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester
CAS No.:197567-54-7
Molecular Formula:C₂₅H₃₇NO₈
Molecular Weight:479.571
Hs Code.:

(S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

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Chemical Property of (S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

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Technology Process of (S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

There total 7 articles about (S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl 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:

: 30694-84-9
2,3-4,5-di-O-isopropylidene-D-xylonic acid methyl ester

: 197567-54-7
(S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 55 percent / AcOH / H₂O / 1.5 h / 60 °C

2: 91 percent / PPh₃, CBr₄ / pyridine / 3.5 h / 55 °C

3: 83 percent / H₂, Et₃N / Raney Ni / methanol / 60 h

4: 92 percent / pyridinium tosylate / CH₂Cl₂ / Ambient temperature

5: KOH / dioxane

6: 1.) HOBT, DCC / 1.) CH₂Cl₂, 2 h, 2.) CH₂Cl₂, room temperature, 3 d

With potassium hydroxide; carbon tetrabromide; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; nickel; In 1,4-dioxane; pyridine; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(97)00877-6

Reference yield:

: 187144-41-8
2,3-O-isopropylidene-D-xylonic acid methyl ester

: 197567-54-7
(S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / PPh₃, CBr₄ / pyridine / 3.5 h / 55 °C

2: 83 percent / H₂, Et₃N / Raney Ni / methanol / 60 h

3: 92 percent / pyridinium tosylate / CH₂Cl₂ / Ambient temperature

4: KOH / dioxane

5: 1.) HOBT, DCC / 1.) CH₂Cl₂, 2 h, 2.) CH₂Cl₂, room temperature, 3 d

With potassium hydroxide; carbon tetrabromide; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; nickel; In 1,4-dioxane; pyridine; methanol; dichloromethane;
DOI:10.1016/S0040-4020(97)00877-6

Reference yield:

: 197567-51-4
(4R,5S)-5-((S)-2-Bromo-1-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

: 197567-54-7
(S)-3-Benzyloxy-2-({(4R,5S)-2,2-dimethyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-[1,3]dioxolane-4-carbonyl}-amino)-2-methyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / H₂, Et₃N / Raney Ni / methanol / 60 h

2: 92 percent / pyridinium tosylate / CH₂Cl₂ / Ambient temperature

3: KOH / dioxane

4: 1.) HOBT, DCC / 1.) CH₂Cl₂, 2 h, 2.) CH₂Cl₂, room temperature, 3 d

With potassium hydroxide; hydrogen; pyridinium p-toluenesulfonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; nickel; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1016/S0040-4020(97)00877-6