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

Base Information

• Chemical Name: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 158468-93-0
• Molecular Formula: C₈H₁₆O₆S
• Molecular Weight: 240.277
• Mol file: 158468-93-0.mol

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

Chemical Property of (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol

There total 8 articles about (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)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: 100.0%

2-thioethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (358750-84-2) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol (158468-93-0,130263-77-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1002/anie.201703929

Reference yield: 93.0%

2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside (212309-05-2) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol (158468-93-0,130263-77-3)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1039/b503843j

Reference yield:

2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (16977-78-9,85193-55-1,86651-40-3,86651-32-3) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol (158468-93-0,130263-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / butan-2-one / 3 h / Heating

2: 93 percent / NaOMe / methanol

With sodium methylate; In methanol; butanone;

DOI:10.1039/b503843j

upstream raw materials:

2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside

2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

per-O-acetyl-α-D-mannopyranose

alpha-D-mannopyranoside