(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

Base Information

Chemical Name:(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
CAS No.:181271-03-4
Molecular Formula:C₄₀H₄₈O₉Si
Molecular Weight:700.901
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 80.0%

: [(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6S)-3,4-bis-methoxymethoxy-6-methoxymethoxymethyl-5-trimethylgermanylethynyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylethynyl]-trimethyl-silane

: 181271-03-4
(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

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; methanol; at 40 ℃; for 48h;
DOI:10.1002/hlca.19960790505

Reference yield:

: 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

: 181271-03-4
(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

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 ℃; for 0.833333h;
DOI:10.1002/hlca.19960790505

Reference yield:

: 84218-71-3,114079-12-8,127874-07-1,127875-24-5,127875-31-4,127875-37-0
4-O-acetyl-2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 181271-03-4
(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

Guidance literature:: Multi-step reaction with 5 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

5: 16 g / DIBAH / tetrahydrofuran; toluene / 0.83 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