methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

Base Information

Chemical Name:methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate
CAS No.:891193-82-1
Molecular Formula:C₃₀H₃₀O₆
Molecular Weight:486.565
Hs Code.:

Synonyms:methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

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Chemical Property of methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

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Technology Process of methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

There total 3 articles about methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate 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: 72.0%

: 122059-90-9
methyl (Z)-3-{(4S,5R)-5-[(1R)-1-hydroxy-2-(trityloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propenoate

: 891193-82-1
methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

Guidance literature:: With dipyridinium dichromate; 3 A molecular sieve; acetic acid; In dichloromethane; at 25 ℃; for 0.5h;
DOI:10.1016/j.tetasy.2006.02.006

Reference yield:

: 54503-64-9,54503-65-0
2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

: 891193-82-1
methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / benzoic acid / CH₂Cl₂ / 18 h / Heating

2: 72 percent / pyridinium dichromate; molecular sieves 3 Angstroem; acetic acid / CH₂Cl₂ / 0.5 h / 25 °C

With dipyridinium dichromate; 3 A molecular sieve; acetic acid; benzoic acid; In dichloromethane; 1: Wittig olefination;
DOI:10.1016/j.tetasy.2006.02.006

Reference yield:

: 76-83-5
trityl chloride

: 891193-82-1
methyl (Z)-3-{(4S,5S)-2,2-dimethyl-5-[2-(trityloxy)acetyl]-1,3-dioxolan-4-yl}-2-propenoate

Guidance literature:: Multi-step reaction with 3 steps

1: 69 percent / triethylamine; DMAP / dimethylformamide / 24 h / 0 - 20 °C

2: 91 percent / benzoic acid / CH₂Cl₂ / 18 h / Heating

3: 72 percent / pyridinium dichromate; molecular sieves 3 Angstroem; acetic acid / CH₂Cl₂ / 0.5 h / 25 °C

With dmap; dipyridinium dichromate; 3 A molecular sieve; acetic acid; triethylamine; benzoic acid; In dichloromethane; N,N-dimethyl-formamide; 2: Wittig olefination;
DOI:10.1016/j.tetasy.2006.02.006