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

Base Information

• Chemical Name: 3,5(R)-O-benzylidene-6,7-O-isopropylidene-1-methanesulphonyl-D-glycero-D-gulitol
• CAS No.: 881302-93-8
• Molecular Formula: C₁₈H₂₆O₉S
• Molecular Weight: 418.465
• Mol file: 881302-93-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 3,5(R)-O-benzylidene-6,7-O-isopropylidene-1-methanesulphonyl-D-glycero-D-gulitol 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: 72.0%

(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 + methanesulfonyl chloride (124-63-0) → 3,5(R)-O-benzylidene-6,7-O-isopropylidene-1-methanesulphonyl-D-glycero-D-gulitol (881302-93-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1016/j.jorganchem.2005.10.036

Reference yield: 87.0%

3,5(R)-O-benzylidene-6,7-O-isopropylidene-1-methanesulphonyl-D-glycero-D-gulitol (881302-93-8) → 3,5(R)-O-benzylidene-1-deoxy-6,7-O-isopropylidene-1-iodo-D-glycero-D-gulitol (881302-94-9)

Guidance literature:

With sodium iodide; In butanone; for 1.5h; Heating;

DOI:10.1016/j.jorganchem.2005.10.036

Reference yield:

3,5(R)-O-benzylidene-6,7-O-isopropylidene-1-methanesulphonyl-D-glycero-D-gulitol (881302-93-8) → 1,4:2,5-dianhydro-3-O-benzyl-6-phenyl-D-glycero-D-gulitol

Guidance literature:

Multi-step reaction with 6 steps

1.1: 87 percent / NaI / butan-2-one / 1.5 h / Heating

2.1: 86 percent / Zn-Cu / acetone; H₂O / 1.5 h / Heating

3.1: 92 percent / aq. AcOH / 13.5 h / 20 °C

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

4.2: 21 percent / tetrahydrofuran / 20 °C

5.1: 63 percent / NaBH₃CN; TiCl₄ / acetonitrile / 24 h / 0 - 20 °C

6.1: 71 percent / CuCl₂; AcONa / PdCl₂ / acetic acid / 26 h / 50 °C

With sodium periodate; sodium acetate; titanium tetrachloride; copper; sodium cyanoborohydride; acetic acid; sodium iodide; copper dichloride; zinc; palladium dichloride; In methanol; water; acetic acid; acetone; acetonitrile; butanone;

DOI:10.1016/j.jorganchem.2005.10.036

upstream raw materials:

methanesulfonyl chloride

Downstream raw materials:

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

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