5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole
• CAS No.: 875303-27-8
• Molecular Formula: C₄₄H₅₀N₄O₁₀S
• Molecular Weight: 826.968

Synonyms:5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole

Chemical Property of 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole

There total 20 articles about 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole 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:

(E)-(S)-4-Hydroxy-4-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid tert-butyl ester (875303-35-8) → 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole (875303-27-8)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 100 percent / Et₃N; DMAP

2.1: 100 percent / imidazole; DMAP / dimethylformamide / 50 °C

3.1: 95 percent / DIBAL-H; NaBH₄ / CH₂Cl₂; tetrahydrofuran; methanol

4.1: 99 percent / i-Pr₂NEt; Bu₄NI

5.1: 93 percent / NBS / dimethylsulfoxide; H₂O / 20 °C

6.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

7.1: Hg(OAc)2

7.2: 75 percent / aq. NaBH₄ / tetrahydrofuran / 0 °C

8.1: 91 percent / 18-Cr-6; KHMDS

9.1: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

10.1: 82 percent / Ti(O-i-Pr)4; t-BuOOH; (-)-diisopropyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂

11.1: 84 percent / TBAF / tetrahydrofuran / 20 °C

12.1: 89 percent / pyridine / benzonitrile

13.1: 94 percent / i-Pr₂NEt / CHCl₃ / 40 °C

14.1: 98 percent / AD-mix-β; aq. CH3SO2NH2 / 2-methyl-propan-2-ol

15.1: 86 percent / PPTS

16.1: 90 percent / TBAF / tetrahydrofuran / 55 °C

17.1: DIAD; PPh₃

18.1: H₂O₂; Mo₇O₂₄(NH₄)6

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; ammonium molybdate tetrahydrate; (-)-diisopropyl tartrate; 18-crown-6 ether; methanesulfonamide; di-isopropyl azodicarboxylate; AD-mix-β; mercury(II) diacetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide; benzonitrile; N,N-dimethyl-formamide; tert-butyl alcohol; 11.1: Sharpless asymmetric epoxidation / 18.1: Mitsunobu reaction;

DOI:10.1055/s-2005-918960

Reference yield:

(E)-(S)-4-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-hydroxy-but-2-enoic acid tert-butyl ester (875303-36-9) → 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole (875303-27-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 100 percent / imidazole; DMAP / dimethylformamide / 50 °C

2.1: 95 percent / DIBAL-H; NaBH₄ / CH₂Cl₂; tetrahydrofuran; methanol

3.1: 99 percent / i-Pr₂NEt; Bu₄NI

4.1: 93 percent / NBS / dimethylsulfoxide; H₂O / 20 °C

5.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

6.1: Hg(OAc)2

6.2: 75 percent / aq. NaBH₄ / tetrahydrofuran / 0 °C

7.1: 91 percent / 18-Cr-6; KHMDS

8.1: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9.1: 82 percent / Ti(O-i-Pr)4; t-BuOOH; (-)-diisopropyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂

10.1: 84 percent / TBAF / tetrahydrofuran / 20 °C

11.1: 89 percent / pyridine / benzonitrile

12.1: 94 percent / i-Pr₂NEt / CHCl₃ / 40 °C

13.1: 98 percent / AD-mix-β; aq. CH3SO2NH2 / 2-methyl-propan-2-ol

14.1: 86 percent / PPTS

15.1: 90 percent / TBAF / tetrahydrofuran / 55 °C

16.1: DIAD; PPh₃

17.1: H₂O₂; Mo₇O₂₄(NH₄)6

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; ammonium molybdate tetrahydrate; (-)-diisopropyl tartrate; 18-crown-6 ether; methanesulfonamide; di-isopropyl azodicarboxylate; AD-mix-β; mercury(II) diacetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide; benzonitrile; N,N-dimethyl-formamide; tert-butyl alcohol; 10.1: Sharpless asymmetric epoxidation / 17.1: Mitsunobu reaction;

DOI:10.1055/s-2005-918960

Reference yield:

(4S,5R)-5-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (875303-41-6) → 5-{(4S,5R)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethanesulfonyl}-1-phenyl-1H-tetrazole (875303-27-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Hg(OAc)2

1.2: 75 percent / aq. NaBH₄ / tetrahydrofuran / 0 °C

2.1: 91 percent / 18-Cr-6; KHMDS

3.1: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4.1: 82 percent / Ti(O-i-Pr)4; t-BuOOH; (-)-diisopropyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂

5.1: 84 percent / TBAF / tetrahydrofuran / 20 °C

6.1: 89 percent / pyridine / benzonitrile

7.1: 94 percent / i-Pr₂NEt / CHCl₃ / 40 °C

8.1: 98 percent / AD-mix-β; aq. CH3SO2NH2 / 2-methyl-propan-2-ol

9.1: 86 percent / PPTS

10.1: 90 percent / TBAF / tetrahydrofuran / 55 °C

11.1: DIAD; PPh₃

12.1: H₂O₂; Mo₇O₂₄(NH₄)6

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; ammonium molybdate tetrahydrate; (-)-diisopropyl tartrate; 18-crown-6 ether; methanesulfonamide; di-isopropyl azodicarboxylate; AD-mix-β; mercury(II) diacetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; chloroform; benzonitrile; tert-butyl alcohol; 5.1: Sharpless asymmetric epoxidation / 12.1: Mitsunobu reaction;

DOI:10.1055/s-2005-918960

upstream raw materials:

(E)-(S)-4-Hydroxy-4-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid tert-butyl ester

(E)-(S)-4-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-hydroxy-but-2-enoic acid tert-butyl ester

(R)-1-{(3aR,4S,6R,7aR)-2,2-Dimethyl-4-[(E)-3-(2-trimethylsilanyl-ethoxymethoxy)-propenyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl}-ethane-1,2-diol

(E)-(S)-4-[(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-(tert-butyl-diphenyl-silanyloxy)-but-2-en-1-ol

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