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

Base Information

• Chemical Name: 2-C-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl) ethyne
• CAS No.: 139195-28-1
• Molecular Formula: C29H30O5
• Molecular Weight: 548.679
• Mol file: 139195-28-1.mol

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

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

Chemical Property:

• PSA: 46.15000
• LogP: 6.36000

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 2-C-(2,3,4,6-Tetra-O-benzyl-a-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: 99.0%

trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane (141100-79-0) → (2R,3R,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyltetrahydropyran (139195-28-1)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo020054m

Reference yield: 89.0%

(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran (139195-27-0) → (2R,3R,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyltetrahydropyran (139195-28-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -80 ℃; for 0.166667h;

DOI:10.1021/jo00022a039

Reference yield: 43.0%

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) + 2-iodoethenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (139195-57-6) → (2R,3R,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyltetrahydropyran (139195-28-1) + (S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester (499135-05-6)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 40 ℃; for 8h; ultrasound irradiation;

2-iodoethenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside; With lithium chloride; In tetrahydrofuran; at -78 - 4 ℃;

DOI:10.1271/bbb.66.2273

upstream raw materials:

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

(trimethylsilylethynyl)tributyltin

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

trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane

Downstream raw materials:

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

(R)-4-[(S)-1-Hydroxy-3-((2R,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

(R)-4-[1-Hydroxy-3-((2R,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

2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-(p-toluenesulfonyl)indole