1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne

Base Information

• Chemical Name: 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne
• CAS No.: 1352617-04-9
• Molecular Formula: C₃₂H₃₄O₈
• Molecular Weight: 546.617
• Mol file: 1352617-04-9.mol

Synonyms:1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne

Chemical Property of 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne

There total 3 articles about 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne 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: 38.0%

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (117174-46-6,53931-27-4) → 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne (1352617-04-9)

Guidance literature:

With copper(l) iodide; C₂₃H₂₇NO₅; In acetonitrile; at 0 - 20 ℃; for 5.25h; basic conditions;

DOI:10.1002/ejoc.201100953

Reference yield: 10.0%

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (117174-46-6,53931-27-4) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne (1352617-04-9) + (2R,3R,4R)-3,4-bis(benzyloxy)-6-[(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl]-2-(benzyloxymethyl)-1-azabicyclo[3.2.0]heptan-7-one (1352616-89-7)

Guidance literature:

With copper(l) iodide; N-cyclohexyl-cyclohexanamine; In acetonitrile; at 0 - 20 ℃; for 5.25h; diastereoselective reaction; basic conditions;

DOI:10.1002/ejoc.201100953

Reference yield:

(2S,3R,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide (950740-50-8) + (3aR,5R,6S,6aR)-6-(benzyloxy)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (117174-46-6,53931-27-4) → 1,4-bis{(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl}buta-1,3-diyne (1352617-04-9) + (2S,3R,4S)-3,4-bis(benzyloxy)-6-[(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl]-2-(benzyloxymethyl)-1-azabicyclo[3.2.0]heptan-7-one (1352616-94-4)

Guidance literature:

With copper(l) iodide; In acetonitrile; at 0 - 20 ℃; for 5.25h; diastereoselective reaction; basic conditions;

DOI:10.1002/ejoc.201100953

upstream raw materials:

(2S,3R,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide

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

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide