RehMapicroside

Base Information

• Chemical Name: RehMapicroside
• CAS No.: 104056-82-8
• Molecular Formula: C16H26 O8
• Molecular Weight: 346.378
• Mol file: 104056-82-8.mol

Synonyms:1-Cyclohexene-1-carboxylicacid, 3-(b-D-glucopyranosyloxy)-2,6,6-trimethyl-,(R)-; Rehmapicroside

Chemical Property of RehMapicroside

Chemical Property:

• Boiling Point: 569.2±50.0 °C(Predicted)
• PKA: 4.53±0.60(Predicted)
• PSA: 136.68000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: -0.60740

Purity/Quality:

99%+, ^*data from raw suppliers

Rehmapicroside >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of RehMapicroside

There total 6 articles about RehMapicroside 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:

methyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate (28120-76-5) → (3R)-2,6,6-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid (104056-82-8)

Guidance literature:

Multi-step reaction with 4 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

4: 33 mg / 10percent aq. KOH / methanol / 12 h / 60 °C

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

DOI:10.1248/cpb.44.41

Reference yield:

methyl 3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate (91029-31-1) → (3R)-2,6,6-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid (104056-82-8)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 0.5percent NaOMe / methanol / 0.25 h / 24 °C

3: 33 mg / 10percent aq. KOH / methanol / 12 h / 60 °C

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

DOI:10.1248/cpb.44.41

Reference yield:

methyl (3R)-3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carboxylate (104112-12-1) → (3R)-2,6,6-trimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carboxylic acid (104056-82-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 8 mg / CrO₃, pyridine / 1 h / 28 °C

2: 6.7 g / NaBH₄ / methanol / 0.33 h / 0 °C

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

4: 0.5percent NaOMe / methanol / 0.25 h / 24 °C

5: 33 mg / 10percent aq. KOH / methanol / 12 h / 60 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; sodium methylate; mercury(II) cyanide; In 1,4-dioxane; methanol; benzene;

DOI:10.1248/cpb.44.41

upstream raw materials:

(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

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

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

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

Downstream raw materials:

(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

methyl D-glucopyranoside

3-Methoxy-2,6,6-trimethyl-cyclohex-1-enecarboxylic acid

(R)-2,6,6-Trimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid

Refernces

• 1、 Yoshikawa,Fukuda,Taniyama. "Absolute configurations of rehmaionosides A, B, and C and rehmapicroside. Three new ionone glucosides and a new monoterpene glucoside from rehmanniae radix". . p. 2294 - 2297. Retrieved 2007/10/02.