5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose

Base Information

• Chemical Name: 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose
• CAS No.: 612830-71-4
• Molecular Formula: C₄₁H₄₁NO₆S
• Molecular Weight: 675.846
• Mol file: 612830-71-4.mol

Synonyms:5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose

Chemical Property of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose

There total 2 articles about 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose 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%

2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde (120520-77-6) + 1-(thiazol-2-yl)-2-(triphenyl-λ 5-phosphanylidene)ethan-1-one (136029-15-7) → 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose (612830-71-4)

Guidance literature:

In chloroform; Heating;

DOI:10.1055/s-2003-39288

Reference yield:

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene (82659-52-7) → 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose (612830-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / 0.67 h / -80 °C

1.2: 71 percent / Me₂S / CH₂Cl₂ / 48 h

2.1: 70 percent / CHCl₃ / 24 h / 60 °C

With ozone; In dichloromethane; chloroform; 2.1: Wittig reaction;

DOI:10.1016/j.tetasy.2004.01.023

Reference yield: 80.0%

methyl (S)-(ethenyloxy)(phenyl)acetate (167702-71-8) + 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-C-(2-thiazolyl)-D-glycero-D-ido-dec-2-enose (612830-71-4) → methyl (S)-2-phenyl-2-({(2R,4R)-4-[(tetra-O-benzyl-α-D-glucopyranosyl)methyl]-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl}oxy)acetate + methyl (R)-2-phenyl-2-({(2S,4S)-4-[(tetra-O-benzyl-α-D-glucopyranosyl)methyl]-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl}oxy)acetate

Guidance literature:

Eu(fod)3; In dichloromethane; at 20 ℃; for 96h;

DOI:10.1135/cccc20051411

upstream raw materials:

2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

1-(thiazol-2-yl)-2-(triphenyl-λ ⁵-phosphanylidene)ethan-1-one

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

Downstream 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

(2S,4S)-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

(2S,4S)-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

(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