1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol

Base Information

• Chemical Name: 1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol
• CAS No.: 190505-05-6
• Molecular Formula: C₃₈H₄₄O₇
• Molecular Weight: 612.763
• Mol file: 190505-05-6.mol

Synonyms:1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol

Chemical Property of 1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol

There total 2 articles about 1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol 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: 59.0%

2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-malonic acid diethyl ester (178931-93-6) → 1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol (190505-05-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(97)00273-1

Reference yield:

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one (179090-11-0) → 1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol (190505-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / Bu₃SnH / tetrahydrofuran / Irradiation

2: 59 percent / LiAlH₄ / tetrahydrofuran

With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(97)00273-1

Reference yield: 94.0%

1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-hydroxymethyl-3-propanol (190505-05-6) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 2-hexadecanoyloxymethyl-3-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester (190505-08-9)

Guidance literature:

With dmap; In pyridine; Heating;

DOI:10.1016/S0040-4020(97)00273-1

upstream raw materials:

2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-malonic acid diethyl ester

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one

Downstream raw materials:

Hexadecanoic acid 2-hexadecanoyloxymethyl-3-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester