(E)-3-Phenyl-3-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-Phenyl-3-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester
• CAS No.: 139293-32-6
• Molecular Formula: C₄₅H₄₆O₈
• Molecular Weight: 714.855
• Mol file: 139293-32-6.mol

Synonyms:

Chemical Property of (E)-3-Phenyl-3-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-Phenyl-3-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester

There total 2 articles about (E)-3-Phenyl-3-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester 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:

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) + phenylpropynoic acid ethyl ester (2216-94-6) → (E)-3-Phenyl-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester (139293-32-6,139293-34-8,139293-36-0,139325-44-3)

Guidance literature:

With sodium hydride; Multistep reaction; 1) THF, 0.5 h, 2) THF, 50 deg C, 3 h;

DOI:10.1016/S0040-4020(01)96047-8

Reference yield:

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) + phenylpropynoic acid ethyl ester (2216-94-6) → (E)-3-Phenyl-3-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester (139293-32-6,139293-34-8,139293-36-0,139325-44-3)

Guidance literature:

With sodium hydride; Multistep reaction; 1) THF, 0.5 h, 2) THF, 50 deg C, 3 h;

DOI:10.1016/S0040-4020(01)96047-8

Reference yield: 90.0%

(E)-3-Phenyl-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester (139293-32-6,139293-34-8,139293-36-0,139325-44-3) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside (151909-91-0)

Guidance literature:

trifluoromethanesulfonate; In acetonitrile; at -40 - -20 ℃; for 3h;

DOI:10.1016/S0040-4020(01)96047-8

upstream raw materials:

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

phenylpropynoic acid ethyl ester

2,3,4,6-tetra-O-benzyl-D-galactopyranose

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside

methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-α-D-glucopyranoside