3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol

Base Information

• Chemical Name: 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol
• CAS No.: 881302-99-4
• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.365
• Mol file: 881302-99-4.mol

Synonyms:3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol

Chemical Property of 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol

There total 5 articles about 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol 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: 41.0%

3,5(S)-O-benzylidene-1,2-dideoxy-D-gluco-1-heptenitol (881302-96-1) + phenylmagnesium bromide → 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol (881302-99-4) + 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-L-ido-1-hexenitol (881302-98-3)

Guidance literature:

3,5(S)-O-benzylidene-1,2-dideoxy-D-gluco-1-heptenitol; With sodium periodate; In methanol; water; at 20 ℃; for 1.5h;

phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.jorganchem.2005.10.036

Reference yield:

3,5(S)-O-benzylidene-1,2-dideoxy-6,7-O-isopropylidene-D-gluco-1-heptenitol (881302-95-0) → 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol (881302-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / aq. AcOH / 13.5 h / 20 °C

2.1: NaIO₄ / methanol; H₂O / 1.5 h / 20 °C

2.2: 21 percent / tetrahydrofuran / 20 °C

With sodium periodate; acetic acid; In methanol; water;

DOI:10.1016/j.jorganchem.2005.10.036

Reference yield:

(S)-1-[(2S,4S,5R,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl]-ethane-1,2-diol → 3,5(S)-O-benzylidene-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol (881302-99-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 72 percent / Et₃N / CH₂Cl₂ / 18 h / 20 °C

2.1: 87 percent / NaI / butan-2-one / 1.5 h / Heating

3.1: 86 percent / Zn-Cu / acetone; H₂O / 1.5 h / Heating

4.1: 92 percent / aq. AcOH / 13.5 h / 20 °C

5.1: NaIO₄ / methanol; H₂O / 1.5 h / 20 °C

5.2: 21 percent / tetrahydrofuran / 20 °C

With sodium periodate; copper; acetic acid; triethylamine; sodium iodide; zinc; In methanol; dichloromethane; water; acetone; butanone;

DOI:10.1016/j.jorganchem.2005.10.036

upstream raw materials:

3,5(S)-O-benzylidene-1,2-dideoxy-D-gluco-1-heptenitol

3,5(S)-O-benzylidene-1,2-dideoxy-6,7-O-isopropylidene-D-gluco-1-heptenitol

3,5(R)-O-benzylidene-1-deoxy-6,7-O-isopropylidene-1-iodo-D-glycero-D-gulitol

3,5(R)-O-benzylidene-6,7-O-isopropylidene-1-methanesulphonyl-D-glycero-D-gulitol

Downstream raw materials:

3-O-benzyl-1,2-dideoxy-6-phenyl-D-gluco-1-hexenitol