1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol

Base Information

• Chemical Name: 1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol
• CAS No.: 876396-84-8
• Molecular Formula: C₂₅H₃₂O₅S
• Molecular Weight: 444.592
• Mol file: 876396-84-8.mol

Synonyms:1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol

Chemical Property of 1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol

There total 1 articles about 1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol 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:

(3S,4S,5S)-3,4-di(benzyloxy)-5-formylthiolane (870462-01-4) + 2-(2-Bromoethyl)-1,3-dioxane (33884-43-4) → 1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol (876396-84-8) + (S)-1-((2R,3S,4S)-3,4-Bis-benzyloxy-tetrahydro-thiophen-2-yl)-3-[1,3]dioxan-2-yl-propan-1-ol

Guidance literature:

2-(2-Bromoethyl)-1,3-dioxane; With magnesium; In tetrahydrofuran;

(3S,4S,5S)-3,4-di(benzyloxy)-5-formylthiolane; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1021/jo052111s

Reference yield: 92.0%

1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol (876396-84-8) + benzyl bromide (100-39-0) → 1,4-anhydro-6,7-dideoxy-2,3,5-tri-O-benzyl-4-thio-7-(1,3-dioxalan-2-yl)-D-altro-septitol (876396-85-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo052111s

Reference yield:

1,4-anhydro-6,7-dideoxy-2,3-di-O-benzyl-4-thio-7-(1,3-dioxolan-2-yl)-D-altro-septitol (876396-84-8) → (4R)-1,4-anhydro-2,3-di-O-benzyl-4-((2R)-tetrahydrofuran-2-yl)-1,4-[benzylepisulfoniumylidene]-D-threitol triflate

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / NaH / dimethylformamide / 2 h / 20 °C

2: acetic acid; H₂SO₄ / H₂O; dioxane / 20 h / 20 °C

3: 0.62 g / NaBH₄ / aq. ethanol / 1 h / cooling

4: 48 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium tetrahydroborate; sulfuric acid; sodium hydride; acetic acid; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo052111s

upstream raw materials:

(3S,4S,5S)-3,4-di(benzyloxy)-5-formylthiolane

2-(2-Bromoethyl)-1,3-dioxane

Downstream raw materials:

1,4-anhydro-6,7-dideoxy-2,3,5-tri-O-benzyl-4-thio-7-(1,3-dioxalan-2-yl)-D-altro-septitol

1,4-anhydro-8-bromo-6,7,8-trideoxy-2,3,5-tri-O-benzyl-4-thio-D-altro-octitol

1,4-anhydro-2,3,5-tri-O-benzyl-6,7-dideoxy-1-thio-D-altro-octitol