1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

Base Information

• Chemical Name: 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside
• CAS No.: 125411-99-6
• Molecular Formula: C36H40O5S
• Molecular Weight: 584.777
• Hs Code.: 2938909090
• Mol file: 125411-99-6.mol

Synonyms:1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside;1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside;1-S-Ethyl 2,3,4,6-tetra-o-benzyl-beta-d-thiogalactopyranoside;Ethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-beta-D-galactopyranoside

Chemical Property of 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

Chemical Property:

• Boiling Point: 691.2±55.0 °C(Predicted)
• PSA: 71.45000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 7.43740
• Storage Temp.: 2-8°C

Purity/Quality:

98%, ^*data from raw suppliers

Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside ^*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-benzyl-b-D-thiogalactopyranoside (CAS# 125411-99-6) is used in the preparation of disaccharides and oligosaccharides via stereoselective 3,3-difluoroxindole-catalyzed regenerative glycosylation.

Technology Process of 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

There total 33 articles about 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside 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: 94.0%

ethyl 1-thio-α-D-mannopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) + benzyl bromide (100-39-0) → S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside (74666-83-4,105990-37-2,108739-67-9,125354-47-4,125411-99-6,125354-46-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 4h;

Reference yield: 92.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4) + ethanethiol (75-08-1) → 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9)

Guidance literature:

With sodium hydride; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.12.105

Reference yield: 88.0%

benzyl bromide (100-39-0) + ethyl 1-thio-β-D-galactopyranoside (56245-60-4,686299-00-3) → ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (125411-99-6)

Guidance literature:

ethyl 1-thio-β-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1080/07328300802408843

upstream raw materials:

benzyl bromide

ethyl 1-thio-β-D-glucopyranoside

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

ethanethiol

Downstream raw materials:

dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

ethyl 2,3,4,6-tetra-O-benzyl-S-(N-tosylimino)-1-thio-β-D-glucopyranoside

Acetic acid (2R,4aR,6R,7R,8S,8aR)-6-bromo-2-phenyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Acetic acid (2R,4aR,6S,7R,8S,8aR)-6-ethylsulfanyl-2-phenyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Refernces

• 1、 -. "Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof". Paragraph 0033; 0057; 0061. . Retrieved 2021/04/03.
• 2、 Krumb, Matthias,Lucas, Tobias,Opatz, Till. "Visible Light Enables Aerobic Iodine Catalyzed Glycosylation". supporting information. p. 4517 - 4521. Retrieved 2019/08/06.