2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne

Base Information

• Chemical Name: 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne
• CAS No.: 168253-07-4
• Molecular Formula: C29H30O5
• Molecular Weight: 548.679
• Mol file: 168253-07-4.mol

Synonyms:2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne;3,7-Anhydro-1,2-dideoxy-4,5,6,8-tetrakis-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol

Chemical Property of 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne

Chemical Property:

• PSA: 46.15000
• LogP: 6.36000

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne

There total 9 articles about 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne 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%

trimethyl(((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)ethynyl)silane (141196-28-3,141100-79-0) → (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran (168253-07-4)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/jo980442h

Reference yield:

Br(1-)*C36H35O6(1-)*Mg(2+) → (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran (168253-07-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 5h;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran (168253-07-4)

Guidance literature:

Multi-step reaction with 3 steps

2: Et₃SiH, BF₃*OEt₂

3: 95 percent / TBAF

With triethylsilane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride;

DOI:10.1021/jo980442h

upstream raw materials:

trimethyl(((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)ethynyl)silane

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-D-glucopyranoside

C₃₉H₄₄O₆Si

Downstream raw materials:

(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-iodo-phenylethynyl)-tetrahydro-pyran

1,1'-(1,2-phenylene)bis[3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-gulo-octitol]

(R)-4-[(S)-1-Hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

1,8-bis[(trimethylsilyl)ethynyl]-9,10-anthraquinone

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