(1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane
• CAS No.: 180675-68-7
• Molecular Formula: C₂₂H₁₈F₄O₄
• Molecular Weight: 422.376
• Mol file: 180675-68-7.mol

Synonyms:(1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property of (1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane

There total 1 articles about (1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane 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: 94.0%

2,6-Difluorobenzyl bromide (85118-00-9) + 1,6-anhydro-4-deoxy-4-C-ethynyl-β-D-glucopyranose (167646-64-2) → (1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane (180675-68-7)

Guidance literature:

With barium dihydroxide; 4 A molecular sieve; In N,N-dimethyl-formamide; for 2.5h; Ambient temperature;

DOI:10.1002/hlca.19960790423

Reference yield: 95.0%

triethylsilyl chloride (994-30-9) + (1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane (180675-68-7) → [(1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-ylethynyl]-triethyl-silane (180675-69-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -76 ℃; for 0.583333h;

DOI:10.1002/hlca.19960790423

Reference yield:

(1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-2-ethynyl-6,8-dioxa-bicyclo[3.2.1]octane (180675-68-7) → Acetic acid (2S,3R,4S,5R,6R)-6-chloro-4,5-bis-(2,6-difluoro-benzyloxy)-3-triethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester (180675-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / BuLi / tetrahydrofuran / 0.58 h / -76 °C

2: 93 percent / methanol / 10 h / 40 °C

With methanol; n-butyllithium; In tetrahydrofuran;

DOI:10.1002/hlca.19960790423

upstream raw materials:

2,6-Difluorobenzyl bromide

1,6-anhydro-4-deoxy-4-C-ethynyl-β-D-glucopyranose

Downstream raw materials:

[(1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-ylethynyl]-triethyl-silane

Acetic acid (2S,3R,4S,5R,6R)-6-chloro-4,5-bis-(2,6-difluoro-benzyloxy)-3-triethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester