(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol
• CAS No.: 869475-37-6
• Molecular Formula: C₄₃H₄₃NO₅S
• Molecular Weight: 685.884
• Mol file: 869475-37-6.mol

Synonyms:(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol

Chemical Property of (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol

There total 1 articles about (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol 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: 32.0%

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone (118206-39-6) + (3-methylindol-1-yl)magnesium bromide → (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol (869475-37-6)

Guidance literature:

In tetrahydrofuran; toluene;

DOI:10.1016/j.tetlet.2005.09.135

Reference yield: 85.0%

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol (869475-37-6) + methyl iodide (74-88-4) → 3-Methyl-1-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-2-yl)-1H-indole

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2005.09.135

Reference yield:

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol (869475-37-6) + trimethoxonium tetrafluoroborate (420-37-1) → 3-Methyl-1-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indole + 3-Methyl-1-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-2-yl)-1H-indole

Guidance literature:

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol; trimethoxonium tetrafluoroborate; In acetonitrile; at -20 ℃;

With sodium tetrahydroborate; In acetonitrile; at -20 - 20 ℃;

DOI:10.1016/j.tetlet.2005.09.135

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone