(2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate

Base Information

• Chemical Name: (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate
• CAS No.: 916069-07-3
• Molecular Formula: C₄₆H₄₂O₁₂
• Molecular Weight: 786.832
• Mol file: 916069-07-3.mol

Synonyms:(2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate

Chemical Property of (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate

There total 15 articles about (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate 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: 99.0%

(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate (916069-06-2) + Trimethyl orthoacetate (1445-45-0) → (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate (916069-07-3)

Guidance literature:

(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate; Trimethyl orthoacetate; With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 0.25h;

With acetic acid; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/ol062076r

Reference yield: 99.0%

(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate (916069-06-2) + acetic acid (64-19-7,77671-22-8) → (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate (916069-07-3)

Guidance literature:

(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate; With Trimethyl orthoacetate; toluene-4-sulfonic acid;

acetic acid; With water; at 0 ℃; for 1h; regioselective reaction;

DOI:10.1021/acs.orglett.0c00042

Reference yield:

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) → (2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate (916069-07-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / PPh₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

2.1: 73 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

3.1: 156 mg / pyridine; DMAP / CH₂Cl₂ / 1 h / 0 °C

4.1: 77 percent / OsO₄; NMO / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

5.1: p-TsOH*H₂O / CH₂Cl₂ / 0.25 h / 0 °C

5.2: 99 percent / aq. HOAc / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; toluene-4-sulfonic acid; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ol062076r

upstream raw materials:

(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate

Trimethyl orthoacetate

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one

Downstream raw materials:

(2S,3S,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate

Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside)

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Refernces

• 1、 Shan, Mingde,O'Doherty, George A.. "De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation". . p. 5149 - 5152. Retrieved 2007/10/03.