2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol

Base Information

• Chemical Name: 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol
• CAS No.: 220869-68-1
• Molecular Formula: C₃₂H₄₁NO₈SSi
• Molecular Weight: 627.831
• Mol file: 220869-68-1.mol

Synonyms:2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol

Chemical Property of 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol

There total 1 articles about 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol 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:

methanesulfonyl chloride (124-63-0) + tert-butylchlorodiphenylsilane (58479-61-1) + 2-Benzamido-2-deoxy-4,6-O-ethylidene-D-glucitol (157117-17-4) → Methanesulfonic acid (1R,2S)-2-benzoylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-((2R,4S,5R)-5-methanesulfonyloxy-2-methyl-[1,3]dioxan-4-yl)-propyl ester (157117-18-5) + 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol (220869-68-1)

Guidance literature:

With pyridine; Yield given; Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, room temperature, 24 h, 2.) CH₂Cl₂, 0-5 deg C, 5 h;

DOI:10.1016/S0040-4020(98)01104-1

Reference yield: 85.0%

2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol (220869-68-1) → (4R,5R)-4-[(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-2-methyl-[1,3]dioxan-5-ol

Guidance literature:

With pyridine; triethylamine; In toluene; at 110 ℃; for 24h;

DOI:10.1016/S0040-4020(98)01104-1

Reference yield:

2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol (220869-68-1) → (2S,3S,4R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-hexadecanoylaminooctadecane-1,3,4-triol (220869-81-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / pyridine, triethylamine / toluene / 24 h / 110 °C

2: 84 percent / thiophenol, TiCl₄ / CH₂Cl₂ / 1 h / -15 - -10 °C / other reagent: BF₃*OEt₂

3: NaIO₄ / methanol; H₂O / 2 h / 5 - 10 °C

4: 50 percent / ZnCl₂, tetradecylmagnesium chloride / tetrahydrofuran / -70 - -20 °C / other reagents: BF₃*OEt₂, CeCl₃, reagent absence

5: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

6: 1.) molecular sieves 4A, 2.) silver trifluoromethanesulfonate / 1.) ClCH₂CH₂Cl, room temperature, 30 min, 2.) ClCH₂CH₂Cl, 70 deg C, 15 h

7: 90 percent / 2,2'-azobis(isobutyronitrile), tributyltin hydride / toluene / 1 h / 80 °C

8: HCl / tetrahydrofuran; H₂O / 3 h / Ambient temperature

9: 43 mg / triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; hydrogenchloride; sodium periodate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; titanium tetrachloride; thiophenol; triethylamine; n-tetradecylmagnesium chloride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(98)01104-1

upstream raw materials:

methanesulfonyl chloride

tert-butylchlorodiphenylsilane

2-Benzamido-2-deoxy-4,6-O-ethylidene-D-glucitol

Downstream raw materials:

(1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

(4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde

(1R,4'S,5'S)-1-<4'-hydroxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

(1R,2R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>propane-1,2,3-triol