(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

Base Information

• Chemical Name: (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
• CAS No.: 142800-29-1
• Molecular Formula: C₄₉H₅₆O₈Si
• Molecular Weight: 801.064
• Mol file: 142800-29-1.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 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: 75.0%

2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (142800-27-9) + (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) → <(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 (142800-31-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1021/ja00047a077

Reference yield:

(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) → <(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 (142800-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

2: 88 percent / NaOMe / methanol

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/ja00047a077

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

Downstream raw materials:

<(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

<(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