methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate

Base Information

• Chemical Name: methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate
• CAS No.: 149551-08-6
• Molecular Formula: C₃₅H₄₂O₇Si
• Molecular Weight: 602.8
• Mol file: 149551-08-6.mol

Synonyms:methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate

Chemical Property of methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate

There total 1 articles about methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate 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:

(R)-(-)-O-acetylmandelic acid (51019-43-3) + methyl 2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate → methyl (1S,2R,2'R,4R)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate + methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate (149551-08-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 3h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1002/hlca.19930760207

Reference yield: 89.0%

methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate (149551-08-6) → methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (149654-56-8)

Guidance literature:

With sodium methylate; In methanol; for 17h; Ambient temperature;

DOI:10.1002/hlca.19930760207

Reference yield:

methyl (1R,2S,2'R,4S)-t-4-<2'-acetoxy-2'-phenylacetoxy>-t-2-(<(tert-butyl)diphenylsilyloxy>methyl)cyclopentane-r-l-acetate (149551-08-6) → N6-benzoyl-2',3',5'-trideoxy-5'-<(tritylthio)methyl>-1'a-carbaadenylyl-(3'->CH2SCH2->5')-N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / NaOMe / methanol / 17 h / Ambient temperature

3: 69 percent / NH₃ / methanol / 0.5 h / 0 °C

4: 80 percent / pyridine / CH₂Cl₂ / Ambient temperature

5: 91 percent / Bu₄NF * 3 H₂O / tetrahydrofuran / Ambient temperature

6: 100 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

7: 9 mg / DBU / dimethylformamide / Ambient temperature; 1) 5h, 2) 24 h

With pyridine; tetrabutyl ammonium fluoride; ammonia; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19930760207

upstream raw materials:

(R)-(-)-O-acetylmandelic acid

Downstream raw materials:

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine

N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine