(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran
• CAS No.: 1454797-06-8
• Molecular Formula: C₄₇H₄₄O₅
• Molecular Weight: 688.863
• Mol file: 1454797-06-8.mol

Synonyms:(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran

Chemical Property of (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran

There total 3 articles about (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran 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: 95.0%

trityl chloride (76-83-5) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol (153496-00-5) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran (1454797-06-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo401613v

Reference yield:

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran (1454797-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 0.25 h / 0 - 20 °C / Inert atmosphere

3: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; trichlorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: |Vilsmeier-Haack Formylation;

DOI:10.1021/jo401613v

Reference yield:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde (136982-88-2) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran (1454797-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 0.25 h / 0 - 20 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo401613v

upstream raw materials:

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

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde

trityl chloride

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol

Downstream raw materials:

(2S,3S,4R,5S)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)pyrrolidine

(2S,3S,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)pyrrolidine

(2R,3R,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

(2R,3R,4S,5R)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyldimethanesulfonate