((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Base Information

• Chemical Name: ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
• CAS No.: 956485-08-8
• Molecular Formula: C₃₆H₄₂O₆Si
• Molecular Weight: 598.811
• Mol file: 956485-08-8.mol

Synonyms:((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Chemical Property of ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

There total 21 articles about ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 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: 64.0%

((3aR,6S,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5,5-diyl)dimethanol (956485-07-7) + tert-butylchlorodiphenylsilane (58479-61-1) → 4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose (956485-09-9) + ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (956485-08-8)

Guidance literature:

((3aR,6S,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5,5-diyl)dimethanol; tert-butylchlorodiphenylsilane; With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

With methanol; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

((3aR,6S,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5,5-diyl)dimethanol (956485-07-7) + tert-butylchlorodiphenylsilane (58479-61-1) → ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (956485-08-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → 4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose (956485-09-9) + ((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (956485-08-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice

2.1: acetic acid / water / 16 h / 20 °C

3.1: sodium periodate / 1,4-dioxane; water / 1 h

4.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice

5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

5.2: 2 h / 20 °C

With sodium periodate; sodium hydride; acetic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

((3aR,6S,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxole-5,5-diyl)dimethanol

tert-butylchlorodiphenylsilane

2-bromomethylnaphthyl bromide

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose

Downstream raw materials:

C₃₇H₄₂O₆Si

5-O-(tert-butyldiphenylsilyl)-4-C-((R)-1-hydroxyethyl)-1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-α-D-ribofuranose

C₃₈H₄₆O₈SSi

(1S,3R,4R,6S,7S)-1-(tert-butyldiphenylsilyloxymethyl)-6-methyl-7-(2-naphthylmethyloxy)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane