(2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran
• CAS No.: 612830-75-8
• Molecular Formula: C₄₃H₄₈O₈
• Molecular Weight: 692.849
• Mol file: 612830-75-8.mol

Synonyms:(2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran

Chemical Property of (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran

There total 10 articles about (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran 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: 70.0%

(2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-(2-thiazolyl)-3,4-dihydro-2H-pyran (612830-73-6) → (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran (612830-75-8)

Guidance literature:

(2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-(2-thiazolyl)-3,4-dihydro-2H-pyran; With 4 A molecular sieve; methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 0.25h;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.25h;

With silver nitrate; In water; acetonitrile; for 0.166667h;

DOI:10.1016/j.tetasy.2004.01.023

Reference yield:

[(4R,6R)-6-Ethoxy-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-5,6-dihydro-4H-pyran-2-yl]-methanol → (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran (612830-75-8)

Guidance literature:

With silver nitrate; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1055/s-2003-39288

Reference yield:

2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde (120520-77-6) → (2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-formyl-3,4-dihydro-2H-pyran (612830-75-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / CHCl₃ / 24 h / 60 °C

2.1: 44 percent / Eu(fod)3 / CH₂Cl₂ / 7 h / 20 °C / sonification

3.1: molecular sieves 4 Angstroem; methyl triflate / acetonitrile / 0.25 h / 20 °C

3.2: NaBH₄ / methanol / 0.25 h / 20 °C

3.3: 70 percent / AgNO₃ / acetonitrile; H₂O / 0.17 h

With 4 A molecular sieve; methyl trifluoromethanesulfonate; Eu(fod)3; In dichloromethane; chloroform; acetonitrile; 1.1: Wittig reaction / 2.1: hetero-Diels-Alder reaction;

DOI:10.1016/j.tetasy.2004.01.023

upstream raw materials:

(2R,4R)-4-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-ido-heptitol-1'-yl)-2-ethoxy-6-(2-thiazolyl)-3,4-dihydro-2H-pyran

(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene

2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

Downstream raw materials:

(2R,3S,4R,6R)-6-Ethoxy-2-hydroxymethyl-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-ol