Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside(contains up to 20% beta isomer)

Base Information

• Chemical Name: Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside (contains up to 20% beta isomer)
• CAS No.: 79389-52-9
• Molecular Formula: C₁₆H₂₄O₉S
• Molecular Weight: 392.427
• Hs Code.: 2938909090
• Mol file: 79389-52-9.mol

Synonyms:a-D-Mannopyranoside, ethyl1-thio-, tetraacetate (9CI); Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-a-D-mannopyranoside

Chemical Property of Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside(contains up to 20% beta isomer)

Chemical Property:

• Melting Point: 80-85°C
• PSA: 139.73000
• LogP: 0.82260
• Storage Temp.: -20?C Freezer
• Solubility.: Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside| ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside can be used as a useful reagent for the preparation of mannosides.

Technology Process of Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside(contains up to 20% beta isomer)

There total 72 articles about Ethyl 2,3,4,6-Tetra-O-acetyl-a-D-thiomannopyranoside(contains up to 20% beta isomer) 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: 100.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (127753-95-1) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; at -10 ℃;

DOI:10.1039/a909218h

Reference yield: 96.0%

acetyl chloride (75-36-5) + ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2005.11.035

Reference yield: 92.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) + ethanethiol (75-08-1) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

D-Glucose; acetic anhydride; With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

ethanethiol; With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200500646

upstream raw materials:

ethanethiol

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

tri-n-butyltin(SC₂H₅)

Downstream raw materials:

tetra-O-acetyl-1,5-anhydro-D-mannitol

ethyl 1-thio-α-D-mannopyranoside

S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide

ethyl 2,3,4,6-tetra-O-acetyl-S-(N-tosylimino)-1-thio-α-D-mannopyranoside

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