3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H₂]propionic acid methylester

Base Information

• Chemical Name: 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H₂]propionic acid methylester
• CAS No.: 880160-76-9
• Molecular Formula: C₂₂H₃₃O₉P
• Molecular Weight: 474.457

Synonyms:3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H₂]propionic acid methylester

Chemical Property of 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H₂]propionic acid methylester

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Technology Process of 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H₂]propionic acid methylester

There total 5 articles about 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H₂]propionic acid methylester 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:

C16H17(2)H2F3O7S (924266-18-2) + Methyl diethylphosphonoacetate (1067-74-9) → 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H2]propionic acid methylester (880160-76-9)

Guidance literature:

Methyl diethylphosphonoacetate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

C₁₆H₁₇⁽²⁾H₂F₃O₇S; With 15-crown-5; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ja056714x

Reference yield:

((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-[di-2H]methanol (145729-45-9) → 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H2]propionic acid methylester (880160-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / CH₂Cl₂ / 0.25 h / -30 °C

2.1: NaH / dimethylformamide / 0 °C

2.2: 21.0 g / 15-crown -5 / dimethylformamide / 20 °C

With pyridine; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja056714x

Reference yield:

(3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (96150-85-5) → 3-((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-[3,3-2H2]propionic acid methylester (880160-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiAlD₄ / tetrahydrofuran / 0 - 20 °C

2.1: pyridine / CH₂Cl₂ / 0.25 h / -30 °C

3.1: NaH / dimethylformamide / 0 °C

3.2: 21.0 g / 15-crown -5 / dimethylformamide / 20 °C

With pyridine; lithium aluminium deuteride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja056714x

upstream raw materials:

C₁₆H₁₇⁽²⁾H₂F₃O₇S

Methyl diethylphosphonoacetate

((3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-[di-2H]methanol

(3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Downstream raw materials:

methyl [6,6-2H₂]shikimate

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