2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester
• CAS No.: 286372-53-0
• Molecular Formula: C₂₅H₃₆N₄O₄S
• Molecular Weight: 488.651

Synonyms:2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester

There total 10 articles about 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester 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:

(2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-3-trimethylsilanyloxy-pentanal (286372-19-8) → 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester (286372-53-0)

Guidance literature:

Multi-step reaction with 9 steps

1: t-BuLi / diethyl ether

2: K₂CO₃; MeOH

3: MnO₂ / CH₂Cl₂

4: Me₄NBH(OAc)3

5: 91 percent / aq. NaOH; DMPU

6: 100 percent / TBAF

7: PPh₃; DEAD

With methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium carbonate; triphenylphosphine; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; In diethyl ether; dichloromethane; 9: Mitsunobu reaction;

DOI:10.1021/ol991049g

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-oct-6-ene-3,5-diol (286372-48-3) → 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester (286372-53-0)

Guidance literature:

Multi-step reaction with 7 steps

1: MnO₂ / CH₂Cl₂

2: Me₄NBH(OAc)3

3: 91 percent / aq. NaOH; DMPU

4: 100 percent / TBAF

5: PPh₃; DEAD

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; triphenylphosphine; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; In dichloromethane; 7: Mitsunobu reaction;

DOI:10.1021/ol991049g

Reference yield:

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol (168777-81-9) → 2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester (286372-53-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: O₃

1.2: 92 percent / PPh₃

2.1: t-BuLi / diethyl ether

3.1: K₂CO₃; MeOH

4.1: MnO₂ / CH₂Cl₂

5.1: Me₄NBH(OAc)3

6.1: 91 percent / aq. NaOH; DMPU

7.1: 100 percent / TBAF

8.1: PPh₃; DEAD

With methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium carbonate; ozone; triphenylphosphine; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; In diethyl ether; dichloromethane; 11.1: Mitsunobu reaction;

DOI:10.1021/ol991049g

upstream raw materials:

1-Phenyl-1H-tetrazole-5-thiol

2,2-Dimethyl-propionic acid (Z)-3-[(4R,5S,6S)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-but-2-enyl ester

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol

(Z)-3-{(4R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-but-2-en-1-ol

Downstream raw materials:

C₃₈H₅₁N₃SO₈C₂H₄O

(+)-thiazinotrienomycin E

8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one

2,2-Dimethyl-propionic acid (Z)-3-{(4R,5S,6S)-2,2,5-trimethyl-6-[2-(1-phenyl-1H-tetrazole-5-sulfonyl)-ethyl]-[1,3]dioxan-4-yl}-but-2-enyl ester

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