3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose

Base Information

• Chemical Name: 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose
• CAS No.: 120368-01-6
• Molecular Formula: C₁₇H₂₄O₇S
• Molecular Weight: 372.439
• Mol file: 120368-01-6.mol

Synonyms:3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose

Chemical Property of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose

There total 3 articles about 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose 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: 91.0%

3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose (22331-19-7) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose (120368-01-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1139/v90-161

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose (120368-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂

2: 91 percent / LiAlH₄ / tetrahydrofuran

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c39880001525

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose (120368-01-6)

Guidance literature:

Multi-step reaction with 3 steps

1: HCl / H₂O; methanol

2: Et₃N / CH₂Cl₂

3: 91 percent / LiAlH₄ / tetrahydrofuran

With hydrogenchloride; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1039/c39880001525

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

(E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Refernces

• 1、 Shing,Aloui. "Enantiospecific synthesis of (6R, 7S)-diastereoisomer of asperlin". . p. 1035 - 1037. Retrieved 1990.