2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride
• CAS No.: 1392478-89-5
• Molecular Formula: C₅₀H₆₉O₆S*Cl
• Molecular Weight: 833.613
• Mol file: 1392478-89-5.mol

Synonyms:2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride

Chemical Property of 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride

There total 3 articles about 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride 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:

C50H69O6S(1+)*BF4(1-) → 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride (1392478-89-5) + C50H69O6S(1+)*Cl(1-)

Guidance literature:

With ion exchange resins IRA-400 J (Cl^- form); In methanol; water; at 20 ℃;

DOI:10.1016/j.bmc.2016.06.013

Reference yield:

(1S)-2-(benzyloxy)-1-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol (1310460-70-8) → 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride (1392478-89-5) + C50H69O6S(1+)*Cl(1-)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

2: hydrogenchloride / ethanol; water / 0.5 h / Reflux

3: diethylazodicarboxylate; triphenylphosphine / toluene / 4 h / 0 - 20 °C / Reflux

4: tetrafluoroboric acid dimethyl ether complex / dichloromethane / 3 h / -60 °C

5: ion exchange resins IRA-400 J (Cl^- form) / methanol; water / 20 °C

With hydrogenchloride; sodium hydride; triphenylphosphine; tetrafluoroboric acid dimethyl ether complex; diethylazodicarboxylate; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2016.06.013

Reference yield:

benzyl bromide (100-39-0) → 2,3,5-tri-O-benzyl-1,4-{(R)-[1-O-benzyl-4-deoxy-3-O-(tridec-1-yl)-D-erythritol-4-yl]episulfoniumylidene}-1,4-dideoxy-D-arabinitol chloride (1392478-89-5) + C50H69O6S(1+)*Cl(1-)

Guidance literature:

Multi-step reaction with 6 steps

1.1: di(n-butyl)tin oxide / toluene / 1 h / Dean-Stark; Reflux

1.2: 1 h / 60 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

3.1: hydrogenchloride / ethanol; water / 0.5 h / Reflux

4.1: diethylazodicarboxylate; triphenylphosphine / toluene / 4 h / 0 - 20 °C / Reflux

5.1: tetrafluoroboric acid dimethyl ether complex / dichloromethane / 3 h / -60 °C

6.1: ion exchange resins IRA-400 J (Cl^- form) / methanol; water / 20 °C

With hydrogenchloride; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; tetrafluoroboric acid dimethyl ether complex; diethylazodicarboxylate; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2016.06.013

upstream raw materials:

(1S)-2-(benzyloxy)-1-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

benzyl bromide