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

Base Information

Chemical Name:(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol
CAS No.:181270-94-0
Molecular Formula:C₃₂H₃₈O₅Si
Molecular Weight:530.736
Hs Code.:

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

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

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

There total 3 articles about (2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol 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%

: 181270-93-9
Acetic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-yl ester

: 181270-94-0
(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 ℃; for 1h;
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

: 181270-94-0
(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 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

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/hlca.19960790505

Reference yield:

: 181270-92-8
Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

: 181270-94-0
(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

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

2: 95 percent / DIBAH / tetrahydrofuran; toluene / 1 h / 0 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1002/hlca.19960790505