{(4R,5S)-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-yl}-methanol

Base Information

• Chemical Name: {(4R,5S)-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-yl}-methanol
• CAS No.: 875303-52-9
• Molecular Formula: C₃₇H₄₆O₉
• Molecular Weight: 634.767

Synonyms:{(4R,5S)-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-yl}-methanol

Chemical Property of {(4R,5S)-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-yl}-methanol

Chemical Property:

Purity/Quality:

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Technology Process of {(4R,5S)-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-yl}-methanol

There total 18 articles about {(4R,5S)-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-yl}-methanol 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: 90.0%

(2-{(4R,5S)-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-ylmethoxymethoxy}-ethyl)-trimethyl-silane (875303-51-8) → {(4R,5S)-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-yl}-methanol (875303-52-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 55 ℃;

DOI:10.1055/s-2005-918960

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) → {(4R,5S)-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-yl}-methanol (875303-52-9)

Guidance literature:

Multi-step reaction with 17 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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; (-)-diisopropyl tartrate; 18-crown-6 ether; methanesulfonamide; AD-mix-β; mercury(II) diacetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 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;

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) → {(4R,5S)-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-yl}-methanol (875303-52-9)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; N-Bromosuccinimide; (-)-diisopropyl tartrate; 18-crown-6 ether; methanesulfonamide; AD-mix-β; mercury(II) diacetate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 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;

DOI:10.1055/s-2005-918960

upstream raw materials:

(2-{(4R,5S)-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-ylmethoxymethoxy}-ethyl)-trimethyl-silane

(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

Downstream raw materials:

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

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