1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol

Base Information

• Chemical Name: 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol
• CAS No.: 37073-70-4
• Molecular Formula: C₃₅H₃₆O₆
• Molecular Weight: 552.667

Synonyms:1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol

Chemical Property of 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol

Chemical Property:

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Technology Process of 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol

There total 9 articles about 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol 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: 90.0%

(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) + trityl chloride (76-83-5) → 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol (37073-70-4)

Guidance literature:

With pyridine; at 0 - 20 ℃; regioselective reaction;

DOI:10.1002/ejoc.201101815

Reference yield: 90.0%

triphenylmethyl alcohol (76-84-6) + (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) → 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol (37073-70-4)

Guidance literature:

With tris(pentafluorophenyl)borate; In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2007.12.020

Reference yield: 65.0%

trityl chloride (76-83-5) + 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose (42926-89-6) → 3-O-Benzyl-1,2-O-isopropyliden-6-O-triphenylmethyl-α-D-glucofuranose (35777-80-1,37073-70-4,106734-68-3,106734-69-4)

Guidance literature:

With pyridine; for 12h; Inert atmosphere;

DOI:10.1039/c3ra43827a

upstream raw materials:

1,2:5,6-diacetone-D-glucose

3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

trityl chloride

1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose

Downstream raw materials:

Trifluoro-methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-trityloxy-ethyl ester

5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-6-O-trityl-α-D-glucofuranose

3-O-benzyl-1,2-O-isopropylidene-6-O-(triphenylmethyl)-α-D-xylo-hexofuranos-5-ulose

3-O-benzyl-1,2-O-isopropyridene-α-D-glucofuranuronic acid

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