(2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran
• CAS No.: 851392-46-6
• Molecular Formula: C₅₁H₇₄O₇Si₃
• Molecular Weight: 883.401

Synonyms:(2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran

Chemical Property of (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran

There total 5 articles about (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran 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:

Allylchlorodimethylsilane (4028-23-3) → (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran (851392-46-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / pyridine; molecular sieves 3 Angstroem / 1 h / 20 °C

2: 97 percent / Bu₃SnH; AIBN / benzene / 2 h / Heating

3: tetrahydrofuran; diethyl ether / 0.08 h / -20 °C

4: pyridine / 12 h / 20 °C

With pyridine; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1016/j.tet.2005.02.025

Reference yield:

(2R,3R,4R,4aS,9aR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-2-trityloxymethyl-octahydro-1,5-dioxa-6-sila-benzocycloheptene (288585-04-6) → (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran (851392-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; diethyl ether / 0.08 h / -20 °C

2: pyridine / 12 h / 20 °C

With pyridine; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tet.2005.02.025

Reference yield:

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6) → (2R,3S,4R,5R,6R)-3-acetoxy-6-(triphenylmethoxy)methyl-4,5-bis-O-(tert-butyl(dimethyl)silyloxy)-2-[3-(dimethyl(p-methoxyphenyl)silyl)propyl]tetrahydropyran (851392-46-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / pyridine; molecular sieves 3 Angstroem / 1 h / 20 °C

2: 97 percent / Bu₃SnH; AIBN / benzene / 2 h / Heating

3: tetrahydrofuran; diethyl ether / 0.08 h / -20 °C

4: pyridine / 12 h / 20 °C

With pyridine; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1016/j.tet.2005.02.025

upstream raw materials:

acetyl chloride

Allylchlorodimethylsilane

(2R,3R,4R,4aS,9aR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-2-trityloxymethyl-octahydro-1,5-dioxa-6-sila-benzocycloheptene

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-2-[3-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

4,8-anhydro-4-O-acetyl-9-O-triphenylmethyl-2,3-dideoxy-D-glycero-D-ido-nonitol

4,8-anhydro-4-O-acetyl-6,7-di-O-(tert-butyl(dimethyl)silyl)-9-O-triphenylmethyl-2,3-dideoxy-D-glycero-D-ido-nonitol

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