(4R,4aS,6S,7S,7aS)-7-(hydroxymethyl)-4-methyl-3-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside

Base Information

Chemical Name:(4R,4aS,6S,7S,7aS)-7-(hydroxymethyl)-4-methyl-3-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside
CAS No.:108906-56-5
Molecular Formula:C₁₆H₂₆O₉
Molecular Weight:362.377
Hs Code.:

Synonyms:Cyclopenta[c]pyran-3(1H)-one,6-(b-D-glucopyranosyloxy)hexahydro-7-(hydroxymethyl)-4-methyl-,[4R-(4a,4aa,6a,7a,7aa)]-; (-)-Gibboside; Gibboside

Suppliers and Price of (4R,4aS,6S,7S,7aS)-7-(hydroxymethyl)-4-methyl-3-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R,4aS,6S,7S,7aS)-7-(hydroxymethyl)-4-methyl-3-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside

Chemical Property:

Vapor Pressure:3.77E-19mmHg at 25°C
Boiling Point:641.3°C at 760 mmHg
Flash Point:234°C
Density:1.48g/cm³

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (4R,4aS,6S,7S,7aS)-7-(hydroxymethyl)-4-methyl-3-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside

There total 15 articles about (4R,4aS,6S,7S,7aS)-7-(hydroxymethyl)-4-methyl-3-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside 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: 85.0%

: 500102-44-3
(4R,4aS,6S,7S,7aS)-7-Benzyloxymethyl-4-methyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[c]pyran-3-one

: 108906-56-5
(-)-gibboside

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate;
DOI:10.1016/S0040-4039(02)01662-3

Reference yield:

: 74808-09-6
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 108906-56-5
(-)-gibboside

Guidance literature:: Multi-step reaction with 2 steps

1: BF₃*OEt₂; 4 Angstroem MS / CH₂Cl₂ / 3 h / -20 °C

2: 85 percent / H₂ / Pd/C / ethyl acetate; methanol

With 4 Angstroem MS; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4039(02)01662-3

Reference yield:

: 500102-37-4
[(4S,5S)-5-((E)-Buta-1,3-dienyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetaldehyde

: 108906-56-5
(-)-gibboside

Guidance literature:: Multi-step reaction with 12 steps

1.1: 88 percent / LiOH*H₂O; MS 4 Angstroem / tetrahydrofuran / 12 h / Heating

2.1: 90 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 - 20 °C

3.1: NaH / (nBu)4NI / tetrahydrofuran / 12 h / 20 °C

4.1: Et₃Al; Fe(acac)3; DMO / toluene / 3 h / 55 °C

4.2: PPTS / CH₂Cl₂ / 12 h / 20 °C

5.1: O₃; Ph₃P / CH₂Cl₂

6.1: NaBH₄ / methanol

7.1: AcOH / H₂O / 75 °C

8.1: PCC / CH₂Cl₂

9.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

10.1: 85 percent / DDQ / CH₂Cl₂; H₂O

11.1: BF₃*OEt₂; 4 Angstroem MS / CH₂Cl₂ / 3 h / -20 °C

12.1: 85 percent / H₂ / Pd/C / ethyl acetate; methanol

With lithium hydroxide; sodium tetrahydroborate; dimethadione; iron(III)-acetylacetonate; 4 Angstroem MS; MS 4 Angstroem; boron trifluoride diethyl etherate; hydrogen; triethylaluminum; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; palladium on activated charcoal; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; toluene; 1.1: Horner-Emmons olefination, Bonadies conditions;
DOI:10.1016/S0040-4039(02)01662-3