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

Base Information

• Chemical Name: [(1S,2R,3S,4R,5R)-3,4-Bis-(2,6-difluoro-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-ylethynyl]-triethyl-silane
• CAS No.: 180675-69-8
• Molecular Formula: C₂₈H₃₂F₄O₄Si
• Molecular Weight: 536.639
• Mol file: 180675-69-8.mol

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

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

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)-6,8-dioxa-bicyclo[3.2.1]oct-2-ylethynyl]-triethyl-silane

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

2,6-Difluorobenzyl bromide (85118-00-9) → [(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:

Multi-step reaction with 2 steps

1: 94 percent / 4A molecular sieves, Ba(OH)2*8H₂O / dimethylformamide / 2.5 h / Ambient temperature

2: 95 percent / BuLi / tetrahydrofuran / 0.58 h / -76 °C

With barium dihydroxide; n-butyllithium; 4 A molecular sieve; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19960790423

Reference yield:

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)-6,8-dioxa-bicyclo[3.2.1]oct-2-ylethynyl]-triethyl-silane (180675-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 4A molecular sieves, Ba(OH)2*8H₂O / dimethylformamide / 2.5 h / Ambient temperature

2: 95 percent / BuLi / tetrahydrofuran / 0.58 h / -76 °C

With barium dihydroxide; n-butyllithium; 4 A molecular sieve; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19960790423

upstream raw materials:

triethylsilyl chloride

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

2,6-Difluorobenzyl bromide

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

Downstream raw materials:

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