1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

Base Information

• Chemical Name: 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne
• CAS No.: 221044-89-9
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423

Synonyms:1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

Chemical Property of 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

Chemical Property:

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Technology Process of 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

There total 2 articles about 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne 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: 65.0%

2,3:4,6-di-O-isopropylidene-D-mannopyranose (357604-61-6) + lithium phenylacetylide (4440-01-1) → 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne (221044-89-9)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1039/a808848i

Reference yield: 57.0%

2,3:4,6-di-O-isopropylidene-D-mannopyranose (357604-61-6) + phenylacetylene (536-74-3) → 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne (221044-89-9) + 1-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-phenyl-propynol + (4R,5R)-4-[(4R,5R)-5-((S)-1-Hydroxy-3-phenyl-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,2-dimethyl-[1,3]dioxan-5-ol (631917-85-6)

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

2,3:4,6-di-O-isopropylidene-D-mannopyranose; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(03)00532-9

Reference yield: 65.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne (221044-89-9) → 1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne (221044-97-9) + (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-{(4R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,2-dimethyl-[1,3]dioxane

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; Yields of byproduct given;

DOI:10.1039/a808848i

upstream raw materials:

2,3:4,6-di-O-isopropylidene-D-mannopyranose

lithium phenylacetylide

phenylacetylene

Downstream raw materials:

Carbonic acid ethyl ester (R)-1-[(4R,5S)-5-((4R,5R)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-phenyl-prop-2-ynyl ester

1-phenyl-1,2-dideoxy-4,5:6,8-di-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-D-talo-D-glycero-oct-1-yne

(1R,2R,3S,4R,5R)-1,2,3,4-tetra-acetoxy-5-(acetoxymethyl)cyclohexane

2,3:4,6-di-O-isopropylidene-1-O-benzyl-5a-carba-β-D-mannopyranose

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