(4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane

Base Information

• Chemical Name: (4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane
• CAS No.: 426841-71-6
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348

Synonyms:(4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane

Chemical Property of (4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane

Chemical Property:

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Technology Process of (4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane

There total 2 articles about (4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane 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: 91.0%

benzaldehyde dimethyl acetal (1125-88-8) + (3R,5S)-3,5,6-Trihydroxy-hexanoic acid isopropyl ester (426841-76-1) → (4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane (426841-71-6)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-2002-20037

Reference yield:

(3R,5S)-6-benzyloxy-3,5-dihydroxyhexanoic acid isopropyl ester (291506-89-3) → (4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane (426841-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h / 23 °C

2: 91 percent / p-TsOH / CH₂Cl₂ / 1 h / 20 °C

With hydrogen; toluene-4-sulfonic acid; palladium dihydroxide; In dichloromethane; ethyl acetate;

DOI:10.1055/s-2002-20037

Reference yield:

(4S,6R)-6-isopropyloxycarbonylmethyl-4-hydroxymethyl-2-phenyl-1,3-dioxane (426841-71-6) → ((4R,6S)-6-Formyl-2-phenyl-[1,3]dioxan-4-yl)-acetic acid isopropyl ester

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 23 ℃;

DOI:10.1055/s-2002-20037

upstream raw materials:

benzaldehyde dimethyl acetal

(3R,5S)-3,5,6-Trihydroxy-hexanoic acid isopropyl ester

(3R,5S)-6-benzyloxy-3,5-dihydroxyhexanoic acid isopropyl ester

Downstream raw materials:

(4S,6R)-6-isopropyloxycarbonylmethyl-2-phenyl-4-[(E)-3-oxoprop-1-enyl]-1,3-dioxane

(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

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