2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol
• CAS No.: 942610-80-2
• Molecular Formula: C₃₃H₄₀O₉S₂
• Molecular Weight: 644.807
• Mol file: 942610-80-2.mol

Synonyms:2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

Chemical Property of 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

There total 4 articles about 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol 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%

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol (187590-77-8) + 2,4-O-isopropylidene-L-erythritol-1,3-cyclic sulfate (302579-02-8) → 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (942610-80-2)

Guidance literature:

With potassium carbonate; In various solvent(s); for 6h; Heating;

DOI:10.1016/j.bmc.2006.10.014

Reference yield:

benzyl bromide (100-39-0) → 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (942610-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

2: 99 percent / potassium carbonate / various solvent(s) / 6 h / Heating

With sodium hydride; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.10.014

Reference yield:

3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose (160882-25-7) → 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (942610-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

2: 99 percent / potassium carbonate / various solvent(s) / 6 h / Heating

With sodium hydride; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.10.014

upstream raw materials:

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol

2,4-O-isopropylidene-L-erythritol-1,3-cyclic sulfate

benzyl bromide

3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

Downstream raw materials:

(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate