(5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane

Base Information

• Chemical Name: (5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane
• CAS No.: 172751-34-7
• Molecular Formula: C₂₇H₃₄O₆Si
• Molecular Weight: 482.649
• Mol file: 172751-34-7.mol

Synonyms:(5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane

Chemical Property of (5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane

There total 1 articles about (5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane 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:

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose (172751-32-5) → (5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane (172751-34-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MeMgCl, 2.) Mg, dibromoethane

2: 85.7 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

With 1,1-Dibromoethane; 4 A molecular sieve; methylmagnesium chloride; magnesium; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jm950278f

Reference yield: 68.0%

(5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane (172751-34-7) → (5R,6R,9S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-8,9-dihydroxy-1,7-dioxa-spiro[4.4]nonan-2-one

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 11h; Ambient temperature;

DOI:10.1021/jm950278f

Reference yield:

(5S,6R,8S,9S)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-8,9-O-isopropylidene-2-keto-1,7-dioxaspiro<4.4>nonane (172751-34-7) → Formic acid (R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((S)-2-formyl-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / 1 N aq. HCl / tetrahydrofuran / 11 h / Ambient temperature

2: aq. NaIO₄ / methanol / 3.5 h / Ambient temperature

With hydrogenchloride; sodium periodate; In tetrahydrofuran; methanol;

DOI:10.1021/jm950278f

upstream raw materials:

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

Downstream raw materials:

(5R)-5-<(1R)-2-<(tert-butyldimethylsilyl)oxy>-1-hydroxyethyl>-5-<2-(tetradecanoxycarbonyl)-(E)-ethenyl>tetrahydro-2-furanone