(4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose

Base Information

• Chemical Name: (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose
• CAS No.: 142800-28-0
• Molecular Formula: C₄₉H₅₄O₉Si
• Molecular Weight: 815.048
• Mol file: 142800-28-0.mol

Synonyms:(4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose

Chemical Property of (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose

There total 13 articles about (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose 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: 59.0%

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) + fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose (142800-26-8) → (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose (142800-28-0)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; Di-tert-butylpyridine; tin(ll) chloride; In diethyl ether; Heating;

DOI:10.1021/ja00047a077

Reference yield: 8.0%

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) + fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose (142800-26-8) → (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose (142800-28-0) + (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->4)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose

Guidance literature:

With 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; silver perchlorate; tin(ll) chloride; In diethyl ether; benzene; for 48h; Heating;

DOI:10.1021/ja00112a007

Reference yield:

methyl 2,3-di-O-benzyl-6-deoxy-α-L-galactopyranoside (42822-27-5) → (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose (142800-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 68 percent / 80percent HOAc, 1 M aq. HCl / 10 h / 100 °C

3: 99 percent / DAST / tetrahydrofuran / 0.08 h / Ambient temperature

4: 59 percent / AgClO₄, SnCl₂, 2,6-di-tert-butylpyridine, 4A molecular sieves / benzene; diethyl ether / 48 h / Heating

With pyridine; hydrogenchloride; 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; silver perchlorate; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja00112a007

upstream raw materials:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose

methyl 2,3-di-O-benzyl-6-deoxy-α-L-galactopyranoside

benzyl bromide