Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate

Base Information

• Chemical Name: Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate
• CAS No.: 121614-07-1
• Molecular Formula: C₂₂H₃₇NO₅Si
• Molecular Weight: 423.625

Synonyms:

Chemical Property of Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate

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Technology Process of Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate

There total 4 articles about Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate 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:

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → Methyl (3R,4S)-3--4,5-(isopropylidenedioxy)-pentanoate (121614-06-0) + Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate (121614-07-1)

Guidance literature:

With zinc(II) fluoride; In dichloromethane; acetonitrile; at -78 ℃; Yield given. Yields of byproduct given;

Reference yield:

N-benzyl hydroxylalmine (622-30-0) → Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate (121614-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Na₂SO₄, / CH₂Cl₂ / 15 h / Ambient temperature

2: ZnF₂, / CH₂Cl₂; acetonitrile / -78 °C

With zinc(II) fluoride; sodium sulfate; In dichloromethane; acetonitrile;

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate (121614-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Na₂SO₄, / CH₂Cl₂ / 15 h / Ambient temperature

2: ZnF₂, / CH₂Cl₂; acetonitrile / -78 °C

With zinc(II) fluoride; sodium sulfate; In dichloromethane; acetonitrile;

upstream raw materials:

ketene t-butyldimethylsilyl methyl acetal

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

N-benzyl hydroxylalmine

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(S)-3-(Benzyl-hydroxy-amino)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester

(3S,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one

(3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine

1-[(3S,5R)-2-Benzyl-3-((S)-1,2-dihydroxy-ethyl)-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione

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