(6-deoxy-2,3,4-tri-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: (6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose
• CAS No.: 142865-32-5
• Molecular Formula: C₄₉H₅₆O₈Si
• Molecular Weight: 801.064
• Mol file: 142865-32-5.mol

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

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

There total 4 articles about (6-deoxy-2,3,4-tri-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: 61.0%

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) + 2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) → (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-4-ol + (6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose (142865-32-5) + (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-3-ol

Guidance literature:

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

DOI:10.1021/ja00112a007

Reference yield: 52.0%

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) + 2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) → (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-((3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-3-ol (142800-29-1,142865-32-5)

Guidance literature:

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

DOI:10.1021/ja00047a077

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose (142865-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine, DMAP / 8 h / 0 °C

2: 61 percent / AgClO₄, SnCl₂, 2,6-di-tert-butylpyridine, 4A molecular sieves / benzene; diethyl ether / 48 h / Ambient temperature

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

DOI:10.1021/ja00112a007

upstream raw materials:

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

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

tert-butylchlorodiphenylsilane

D-glucal

Downstream raw materials:

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

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