3beta-Hydroxy-5-cholestene3-butyrate

Base Information

• Chemical Name: 3beta-Hydroxy-5-cholestene3-butyrate
• CAS No.: 4196-35-4
• Molecular Formula: C34H35BrO5
• Molecular Weight: 603.553
• DSSTox Substance ID: DTXSID80700213
• Mol file: 4196-35-4.mol

Synonyms:DTXSID80700213;3beta-Hydroxy-5-cholestene3-butyrate;2,3,4-Tri-O-benzyl-6,7,8-trideoxy-8-phenyloctopyranosyl bromide

Chemical Property of 3beta-Hydroxy-5-cholestene3-butyrate

Chemical Property:

• Boiling Point: 667.1±55.0 °C(Predicted)
• PSA: 46.15000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 7.07920
• Storage Temp.: Hygroscopic, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 600.18752
• Heavy Atom Count: 40
• Complexity: 666

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosylBromide90%StabilizedwithCalciumCarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCCC2C(C(C(C(O2)Br)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Bromide is a useful synthetic intermediate. It can be used to prepare glycosyl phenylthiosulfonates (Glyco-PTS), a novel reagents for glycoprotein synthesis. It is also used to synthesize oligosaccharides.

Technology Process of 3beta-Hydroxy-5-cholestene3-butyrate

There total 47 articles about 3beta-Hydroxy-5-cholestene3-butyrate 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: 99.0%

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl picolinate → 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4)

Guidance literature:

With copper(ll) bromide; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00078

Reference yield: 98.0%

2,3,4,6-tetra-O-benzyl-D-glucopyranose → 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4)

Guidance literature:

With hydrogen bromide; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo00252a027

Reference yield: 95.0%

2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (744246-05-7) → 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4)

Guidance literature:

With bromine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2007.12.105

upstream raw materials:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate

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

ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside

Downstream raw materials:

7-(tetra-O-benzyl-β-D-glucopyranosyloxy)-10H-dibenzo[b,f][1,4]oxazepin-11-one

4-(tetra-O-benzyl-β-D-glucopyranosyloxy)-10H-dibenzo[b,f][1,4]oxazepin-11-one

2,2,6,6-tetramethylpiperidin-4-yl tetra-O-benzyl-α-D-glucopyranoside hydrobromide

benzyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl)-α-D-glucopyranoside