O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-dimethyl-α-D-glucofuranose

Base Information

• Chemical Name: O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-dimethyl-α-D-glucofuranose
• CAS No.: 39798-98-6
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.401
• Mol file: 39798-98-6.mol

Synonyms:O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-dimethyl-α-D-glucofuranose

Chemical Property of O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-dimethyl-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-dimethyl-α-D-glucofuranose

There total 5 articles about O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-dimethyl-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: 74.5%

(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) + methyl iodide (74-88-4) → O3-benzyl-O1,O2-isopropylidene-O5,O6-dimethyl-α-D-glucofuranose (39798-98-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 8h; Ambient temperature;

DOI:10.1039/c39940001255

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → O3-benzyl-O1,O2-isopropylidene-O5,O6-dimethyl-α-D-glucofuranose (39798-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 0.8percent H₂SO₄ / 12 h / Ambient temperature

2: 74.5 percent / NaH / tetrahydrofuran / 8 h / Ambient temperature

With sulfuric acid; sodium hydride; In tetrahydrofuran;

DOI:10.1039/c39940001255

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) → O3-benzyl-O1,O2-isopropylidene-O5,O6-dimethyl-α-D-glucofuranose (39798-98-6)

Guidance literature:

With silver(l) oxide; methyl iodide;

DOI:10.1021/ja01562a042

upstream raw materials:

(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-O-isopropylidene-α-D-glucofuranose diacetate

methyl iodide

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

Downstream raw materials:

Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((R)-1,2-dimethoxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester