(4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide

Base Information

• Chemical Name: (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide
• CAS No.: 176755-17-2
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293

Synonyms:(4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide

Chemical Property of (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide

Chemical Property:

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Technology Process of (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide

There total 5 articles about (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide 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: 75.0%

(4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide (176755-16-1) → (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide (176755-17-2)

Guidance literature:

With sodium periodate; In 1,4-dioxane; water;

DOI:10.1016/0040-4039(96)00254-7

Reference yield:

O2,O3;O4,O5-diisopropyliden-D-arabinonic acid (30694-81-6) → (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide (176755-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / HNEt₂, DCC / CH₂Cl₂

2: 88 percent / aq. acetic acid / 16 h / 20 °C

3: 75 percent / NaIO₄ / dioxane; H₂O

With sodium periodate; diethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; water; acetic acid;

DOI:10.1016/0040-4039(96)00254-7

Reference yield:

(4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid benzyloxy-amide (176755-14-9) → (4S,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide (176755-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / aq. acetic acid / 16 h / 20 °C

2: 75 percent / NaIO₄ / dioxane; H₂O

With sodium periodate; In 1,4-dioxane; water; acetic acid;

DOI:10.1016/0040-4039(96)00254-7

upstream raw materials:

(4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide

O²,O³;O⁴,O⁵-diisopropyliden-D-arabinonic acid

(4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid benzyloxy-amide

(4R,5S,4'R)-5-(Bis-benzylsulfanyl-methyl)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

Downstream raw materials:

(4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyloxy-amide

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