(2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 79292-19-6
• Molecular Formula: C₂₆H₂₈O₆
• Molecular Weight: 436.505
• Mol file: 79292-19-6.mol

Synonyms:(2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-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: 91.0%

(2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester (79292-18-5) → (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (79292-19-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water;

DOI:10.1016/S0008-6215(00)80681-3

Reference yield:

trityl chloride (76-83-5) → (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (79292-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine / 48 h

2: 91 percent / NaBH₄ / H₂O; tetrahydrofuran

With sodium tetrahydroborate; In tetrahydrofuran; pyridine; water;

DOI:10.1016/S0008-6215(00)80681-3

Reference yield:

3,4,5,7-Tetra-O-acetyl-2,6-anhydro-D-glycero-L-gluco-heptonamide (78393-35-8) → (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (79292-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 7 percent HCl / 24 h / Heating

2: 85 percent / pyridine / 48 h

3: 91 percent / NaBH₄ / H₂O; tetrahydrofuran

With hydrogenchloride; sodium tetrahydroborate; In tetrahydrofuran; pyridine; water;

DOI:10.1016/S0008-6215(00)80681-3

upstream raw materials:

(2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester

trityl chloride

3,4,5,7-Tetra-O-acetyl-2,6-anhydro-D-glycero-L-gluco-heptonamide

methyl 2,6-anhydro-D-glycero-L-gluco-heptonate

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(diisopropoxy-phosphorylmethyl)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-chloromethyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester