117136-33-1

Basic information

• Product Name: 3,4-DI-O-ACETYL-6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• Synonyms: 3,4-DI-O-ACETYL-6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• CAS NO: 117136-33-1
• Molecular Formula: C₁₆H₂₈O₆Si
• Molecular Weight: 378.49
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Aldehydes;Building Blocks;C13-C60;Carbohydrate Chemistry;Carbohydrate Derivatives;Carbonyl Compounds;Chemical Biology;Chemical Synthesis;Organic Building Blocks
• Mol File: 117136-33-1.mol
• Article Data: 5

Chemical Properties

• Flash Point: >230 °F
• Appearance: /
• Density: 1.044 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: ?20°C
• CAS DataBase Reference: 3,4-DI-O-ACETYL-6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DI-O-ACETYL-6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(117136-33-1)
• EPA Substance Registry System: 3,4-DI-O-ACETYL-6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(117136-33-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 117136-33-1(Hazardous Substances Data)

Usage

Uses

Important building block for both solution- and solid-phase synthesis of oligosaccharides.1

Upstream product

• 58871-09-3 6-O-tert-butyldimethylsilyl-D-glucal 
• 75-36-5 acetyl chloride 
• 82295-98-5 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 129840-37-5 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol 
• 1376271-19-0 C₁₇H₂₈O₄Si 
• 1376271-36-1 C₁₇H₂₈O₄Si 
• 250273-58-6 Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-5-allyloxycarbonyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-4-yl ester 
• 250273-61-1 Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-5-allyloxycarbonyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester 
• 250273-59-7 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,6-dimethoxy-phenoxy)-5-hydroxy-tetrahydro-pyran-4-yl ester 
• 250273-62-2 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester 
• 82295-98-5 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol 

Relevant articles and documents

Convenient preparations of 2,3-dihydro-4H-pyran-4-ones from D-glucal triacetate: Selective oxidations of allylic acetates and allylic silyl ethers using N-bromosuccinimide

N-Bromosuccinimide (1.1 eq) in the presence of potassium carbonate (2 eq) and a catalytic amount of dibenzoyl peroxide converts the allylic acetates and the allylic silyl ethers (O-TBDMS or O-SiEt3) of secondary allylic alcohols, derived from D-glucal 3a into corresponding dihydro γ-pyrones 2.

Total synthesis of vancomycin - Part 4: Attachment of the sugar moieties and completion of the synthesis

The total synthesis of vancomycin (1, Figure 1) is described. The successful plan for this synthesis involves sequential and stereoselective coupling of vancomycin aglycon acceptor 6 and glycosyl donors, trichloroacetimidate 50 and glycosyl fluoride 27 (Scheme 8). Acceptor 6 was synthesized from vancomycin aglycon (2) (Scheme 1), which was derived both by total synthesis and by semisynthesis from vancomycin itself (1) (Scheme 2). The vancosamine derivative 27 was obtained by total synthesis (Scheme 3) while the glycosyl derivative 50 was prepared from glucal (46) (Scheme 6). A number of glycosidation model studies, carried out in order to establish the final route to vancomycin (1), are also described and so are a number of failed attempts to secure the target molecule (1).

A New General Route to the Synthesis of Bicyclic Synthons from Glycals

Iodonium sym-dicollidine perchlorate (IDCP: bis(2,4,6-trimethylpyridine)iodine(1+) perchlorate) mediated intramolecular iodoalkoxylation of 3,4-di-O-substituted glycals 9a-14f gives rise to synthetically useful chiral bicyclic synthons 15a-20f respectivel