(4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane
• CAS No.: 1353687-51-0
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 1353687-51-0.mol

Synonyms:(4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane

There total 7 articles about (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane 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: 72.0%

C8H12O3 + benzyl bromide (100-39-0) → (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane (1353687-51-0) + (4S,5R)-4-[(benzyloxy)methyl]-5-ethynyl-2,2-dimethyl-1,3-dioxolane

Guidance literature:

C₈H₁₂O₃; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

benzyl bromide; In tetrahydrofuran;

DOI:10.1002/ejoc.201500395

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane (1353687-51-0)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2011.10.137

Reference yield:

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (78469-77-9,81076-11-1,128820-40-6,78513-03-8) → (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane (1353687-51-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C

1.2: -78 - 20 °C

2.1: potassium carbonate / methanol / 0 - 20 °C

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; In methanol; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Bestmann-Ohira reaction;

DOI:10.1016/j.tetlet.2011.10.137

upstream raw materials:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

Downstream raw materials:

C₂₄H₃₂O₄

C₁₅H₁₇BrO₃

(2R)-5-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-yn-2-ol

(2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate