Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester
• CAS No.: 181270-98-4
• Molecular Formula: C₄₆H₅₄O₁₂Si
• Molecular Weight: 827.013

Synonyms:Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester 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: 86.0%

phenyl 2,3,6-tri-O-acetyl-4-deoxy-4-ethynyl-1-thio-β-d-glucopyranoside (181270-96-2) + (2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol (181270-94-0) → Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester (181270-98-4)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In toluene; at 0 ℃; for 0.0833333h;

DOI:10.1002/hlca.19960790505

Reference yield:

4-O-acetyl-2,3,6-tri-O-benzyl-β-D-glucopyranoside (84218-71-3,114079-12-8,127874-07-1,127875-24-5,127875-31-4,127875-37-0) → Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester (181270-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Dess-Martin's periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1.) BuLi; 2.) BF₃*OEt₂, Et₃SiH / 1.) THF, -78 deg C, 30 min.; 2.) CH₂Cl₂/MeCN, -20 deg C, 10 min.

3: 95 percent / DIBAH / tetrahydrofuran; toluene / 1 h / 0 °C

4: 86 percent / 4 Angstroem molecular sieves, NIS, TfOH / toluene / 0.08 h / 0 °C

With triethylsilane; N-iodo-succinimide; n-butyllithium; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/hlca.19960790505

Reference yield:

1,2,3,6-tetra-O-acetyl-4-deoxy-4-C-ethynyl-α-D-glucopyranose (181270-95-1) → Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester (181270-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / ZnI₂ / CH₂Cl₂ / 4 h / 0 °C

2: 86 percent / 4 Angstroem molecular sieves, NIS, TfOH / toluene / 0.08 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; zinc(II) iodide; In dichloromethane; toluene;

DOI:10.1002/hlca.19960790505

upstream raw materials:

phenyl 2,3,6-tri-O-acetyl-4-deoxy-4-ethynyl-1-thio-β-d-glucopyranoside

(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol

4-O-acetyl-2,3,6-tri-O-benzyl-β-D-glucopyranoside

1,2,3,6-tetra-O-acetyl-4-deoxy-4-C-ethynyl-α-D-glucopyranose

Downstream raw materials:

(2S,3R,4S,5S,6S)-2-((2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-6-hydroxymethyl-tetrahydro-pyran-3,4-diol

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 181270-98-4 Acetic acid (2S,3R,4S,5R,6S)-4-acetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yloxy)-5-ethynyl-tetrahydro-pyran-3-yl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send