(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 39687-20-2
• Molecular Formula: C₃₂H₃₂O₆
• Molecular Weight: 512.602
• Mol file: 39687-20-2.mol

Synonyms:(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

There total 6 articles about (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol 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: 78.0%

trityl chloride (76-83-5) + (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (4304-12-5) → (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (39687-20-2)

Guidance literature:

With dmap; In pyridine; at 60 ℃; for 7h;

DOI:10.1039/b212066f

Reference yield: 37.0%

trityl chloride (76-83-5) + benzyl α-D-galactopyranoside (86196-36-3) → (2S,3R,4S,5S,6R)-2-Benzyloxy-4-trityloxy-6-trityloxymethyl-tetrahydro-pyran-3,5-diol (86172-87-4) + (2R,3R,4S,5R,6S)-6-Benzyloxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol (86172-86-3) + benzyl 6-O-trityl-α-D-galactopyranoside (35017-03-9,39687-20-2,77455-30-2,84396-48-5,86172-88-5)

Guidance literature:

With pyridine; at 100 ℃; for 5h;

DOI:10.1246/bcsj.56.1171

Reference yield:

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate (66966-07-2) → (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (39687-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 20 °C

2: sodium methylate; methanol

3: triethylamine / N,N-dimethyl-formamide / 20 °C

With methanol; boron trifluoride diethyl etherate; sodium methylate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

trityl chloride

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

Downstream raw materials:

benzyl 2,3,4-tri-O-acetyl-6-O-(triphenylmethyl)-β-D-glucopyranoside

(2S,3S,4S,5R,6R)-3,4,5,6-tetrakis(benzyloxy)tetrahydro-2H-pyran-2-carboxylic acid

benzyl 2-O-benzoyl-6-O-trityl-α-D-galactopyranoside

benzyl 3-O-benzoyl-6-O-trityl-α-D-galactopyranoside