(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 287737-63-7
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483
• Mol file: 287737-63-7.mol

Synonyms:(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property of (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

There total 15 articles about (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 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: 86.91%

Methyltriphenylphosphonium bromide (1779-49-3) + (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7) → (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole (287737-63-7)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 1.41h;

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde; In tetrahydrofuran; at 20 ℃; for 20.33h;

Reference yield: 72.0%

iodomethyltriphenylphosphorane + (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7) → (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole (287737-63-7)

Guidance literature:

iodomethyltriphenylphosphorane; With n-butyllithium; In tetrahydrofuran; at 25 - 40 ℃; for 2h;

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde; In tetrahydrofuran; at 0 - 30 ℃; for 2h;

Reference yield: 66.0%

methyl triphenylphosphonium bromide (27200-84-6) + (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7) → (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole (287737-63-7)

Guidance literature:

methyl triphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 1.16667h; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.04.050

upstream raw materials:

Methyltriphenylphosphonium bromide

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

benzyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

2-amino-9-((1R,5R,7R,8S)-8-(benzyloxy)-5-((benzyloxy)methyl)-2,6-dioxabicyclo[3.2.1]octan-7-yl)-1H-purin-6(9H)-one

(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-2,3-diyl diacetate