(4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one

Base Information

• Chemical Name: (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one
• CAS No.: 88096-40-6
• Molecular Formula: C₂₉H₃₄O₄Si
• Molecular Weight: 474.672
• Mol file: 88096-40-6.mol

Synonyms:(4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one

Chemical Property of (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one

There total 13 articles about (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one 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: 70.0%

2,4-dideoxy-3-O-diphenyl-t-butylsilyl-6-O-benzyl-α- and β-D-threo-hexopyranoses (88096-38-2,88096-39-3,116697-28-0) → (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one (88096-40-6)

Guidance literature:

With silver carbonate; In toluene; Heating;

Reference yield:

1,6-anhydro-2,4-dideoxy-3-O-allyl-β-D-threo-hexopyranose (88096-28-0) → (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one (88096-40-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Amberlite IR 118

2: NaH

3: Rh(PPh₃)3Cl

4: CH₃OH, Amberlite IR 118

5: 1.) KH, 2.) formic acid

6: Ag₂CO₃, Celite

With methanol; Wilkinson's catalyst; formic acid; Amberlite IR 118; Celite; potassium hydride; sodium hydride; silver carbonate;

DOI:10.1039/c39830000829

Reference yield:

methyl 2,4-dideoxy-3-O-allyl-α and β-D-threo-hexapyranosides (88096-30-4,88096-31-5) → (4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one (88096-40-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH

2: Rh(PPh₃)3Cl

3: CH₃OH, Amberlite IR 118

4: 1.) KH, 2.) formic acid

5: Ag₂CO₃, Celite

With methanol; Wilkinson's catalyst; formic acid; Amberlite IR 118; Celite; potassium hydride; sodium hydride; silver carbonate;

DOI:10.1039/c39830000829

upstream raw materials:

2,4-dideoxy-3-O-diphenyl-t-butylsilyl-6-O-benzyl-α- and β-D-threo-hexopyranoses

[(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid

benzyl bromide

1,6-anhydro-2,4-dideoxy-3-O-allyl-β-D-threo-hexopyranose

Downstream raw materials:

(2S,4S,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol