2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS No.: 251914-74-6
• Molecular Formula: C₂₃H₂₄O₄
• Molecular Weight: 364.441
• Mol file: 251914-74-6.mol

Synonyms:2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Chemical Property of 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

There total 3 articles about 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 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: 90.0%

benzyl bromide (100-39-0) + (1-prop-2-ynyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (188605-67-6) → 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (251914-74-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jo991044x

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + propargyl alcohol (107-19-7) → prop-2-yn-1-yl 4,6-di-O-benzyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (1388770-51-1) + 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (251914-74-6)

Guidance literature:

With aluminium(III) triflate; In 1,2-dichloro-ethane; at 0 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1039/c2ob25540e

Reference yield:

2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (121237-62-5) → 2-(prop-2-ynyl)-4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (251914-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / water; Et₃N / methanol / 20 °C

2: 90 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 24 h / 20 °C

With water; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; 1: Hydrolysis / 2: Alkylation;

DOI:10.1021/jo991044x

upstream raw materials:

benzyl bromide

(1-prop-2-ynyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

[4aS-(4aα,5β,6α,7aα,7bα)]-5-(benzyloxy)-6-[(benzyloxy)methyl]-5,6,7a,7b-tetrahydro-2H-1,7-dioxacyclopent[cd]inden-4(4aH)-one

Acetic acid (4S,4aR,5S,6R,7aS,7bS)-5-benzyloxy-6-benzyloxymethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-4-yl ester

(4S,4aR,5S,6R,7aS,7bS)-5-Benzyloxy-6-benzyloxymethyl-4,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]inden-4-ol

C₁₇H₂₀O₆