2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester

Base Information

• Chemical Name: 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester
• CAS No.: 240138-00-5
• Molecular Formula: C₄₃H₄₆O₉
• Molecular Weight: 706.833
• Mol file: 240138-00-5.mol

Synonyms:2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester

Chemical Property of 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester

There total 4 articles about 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-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: 84.0%

triphenyl-(α-carbethoxy-β-carboxyethyl)phosphonium betaine (102959-64-8) + (E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenal (240137-99-9) → 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester (240138-00-5)

Guidance literature:

In chloroform; for 10h; Heating;

DOI:10.1055/s-1999-3165

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester (240138-00-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 1.5 h / -78 - 0 °C

2.1: Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

2.2: 65 percent / H₂O / CH₂Cl₂

3.1: 75 percent / MnO₂ / CHCl₃ / 4 h / Heating

4.1: 84 percent / CHCl₃ / 10 h / Heating

With triethylsilane; manganese(IV) oxide; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; chloroform; 1.1: Addition / 2.1: Reduction / 2.2: Hydrolysis / 3.1: Oxidation / 4.1: Wittig reaction;

DOI:10.1055/s-1999-3165

Reference yield:

3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (240137-98-8) → 2-[(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-en-(E)-ylidene]-succinic acid 1-ethyl ester (240138-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / MnO₂ / CHCl₃ / 4 h / Heating

2: 84 percent / CHCl₃ / 10 h / Heating

With manganese(IV) oxide; In chloroform; 1: Oxidation / 2: Wittig reaction;

DOI:10.1055/s-1999-3165

upstream raw materials:

triphenyl-(α-carbethoxy-β-carboxyethyl)phosphonium betaine

(E)-3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propenal

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

3-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol