(S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 104056-89-5
• Molecular Formula: C₁₇H₂₈O₈
• Molecular Weight: 360.405
• Mol file: 104056-89-5.mol

Synonyms:

Chemical Property of (S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester

There total 13 articles about (S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic 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:

2,6,6-Trimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester → (R)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester (104056-89-5) + (S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester (104056-89-5)

Guidance literature:

With sodium methylate; In methanol; for 0.25h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1248/cpb.34.2294

Reference yield:

2,6,6-Trimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester → (R)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester (104056-89-5) + (S)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester (104056-89-5)

Guidance literature:

With sodium methylate; In methanol; for 0.25h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1248/cpb.34.2294

Reference yield:

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate (28120-76-5) → (R)-2,6,6-Trimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester (104056-89-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 6.7 g / NaBH₄ / methanol / 0.33 h / 0 °C

2: Hg(CN)2 / benzene; dioxane / 5 h / Heating

3: 0.5percent NaOMe / methanol / 0.25 h / 24 °C

With sodium tetrahydroborate; sodium methylate; mercury(II) cyanide; In 1,4-dioxane; methanol; benzene;

DOI:10.1248/cpb.44.41

upstream raw materials:

diazomethane

(3R)-2,6,6-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate

methyl 3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

Downstream raw materials:

D-Glucose

methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate

(3R)-2,6,6-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate