(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS No.: 233266-76-7
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 233266-76-7.mol

Synonyms:(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Chemical Property of (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

There total 15 articles about (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 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: 100.0%

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;

Reference yield:

(3aR,5S,6S,6aR)-6-benzyloxy-5-(benzyloxymethyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole → (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7)

Guidance literature:

With sodium periodate; iodine; In water; acetonitrile; at 70 ℃; for 2h; chemoselective reaction;

DOI:10.1021/ol5036535

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / NaH / -5 - 20 °C

2: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; 2: Swern oxidation;

DOI:10.1021/ja071106y

upstream raw materials:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

benzyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

oxalyl dichloride

Downstream raw materials:

3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose

3,5-di-O-benzyl-4-C-ethynyl-1,2-O-isopropylidene-D-ribo-pentofuranose

(((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane

3,5-di-O-benzyl-4-C-(1-hydroxy-allyl)-1,2-O-isopropylidene-α-D-ribofuranose