3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

Base Information

• Chemical Name: 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose
• CAS No.: 140926-87-0
• Molecular Formula: C₃₇H₄₃O₉P
• Molecular Weight: 662.717
• Mol file: 140926-87-0.mol

Synonyms:3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

Chemical Property of 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

There total 2 articles about 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose 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: 95.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + dimethyl methane phosphonate (756-79-6) → 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose (140926-87-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -70 ℃; for 1h;

DOI:10.1021/jo00039a026

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose (140926-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DMSO / acetic anhydride

2: 92 percent / n-BuLi

With n-butyllithium; dimethyl sulfoxide; In acetic anhydride;

DOI:10.1016/S0040-4039(01)01427-7

Reference yield: 94.0%

3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose (140926-87-0) → ((3S,4S,5R,6R)-3,4,5,7-Tetrakis-benzyloxy-2,6-dihydroxy-heptyl)-phosphonic acid dimethyl ester (115250-30-1,115305-00-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1021/jo00039a026

upstream raw materials:

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

dimethyl methane phosphonate

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

((3S,4S,5R,6R)-3,4,5,7-Tetrakis-benzyloxy-2,6-dihydroxy-heptyl)-phosphonic acid dimethyl ester

1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one

validoxylamine G