(2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate

Base Information

• Chemical Name: (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate
• CAS No.: 623148-81-2
• Molecular Formula: C₂₈H₅₀O₇Si₂
• Molecular Weight: 554.872

Synonyms:(2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate

Chemical Property of (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate

There total 22 articles about (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate 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:

benzyl 1-thio-β-D-glucopyranoside (70569-27-6) → (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate (623148-81-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: TsOH / acetonitrile

2.1: 86 percent / NaH; TBAI / dimethylformamide; tetrahydrofuran / 0 - 20 °C

3.1: 95 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; ethanol; H₂O / 3 h / 65 °C

4.1: 70 percent / KOH/alumina; CF₂Br₂ / 2-methyl-propan-2-ol; CH₂Cl₂ / 4 h / 0 - 20 °C

5.1: borane / tetrahydrofuran / 3 h / 0 - 20 °C

5.2: 53 percent / KOH; H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

6.1: 98 percent / iPr₂NEt / CH₂Cl₂ / 10 h / 20 °C

7.1: 85 percent / DDQ / CH₂Cl₂ / 1.5 h / 20 °C

8.1: NaH / dimethylformamide / 0.25 h / 0 °C

8.2: 77 percent / N-tosylimidazole / dimethylformamide / 1.25 h / 0 - 20 °C

9.1: 100 percent / methanol / 20 h / 120 °C

10.1: 100 percent / p-TsOH*H₂O / methanol / 20 °C

11.1: 85 percent / imidazole; PPh₃; I₂ / tetrahydrofuran / 2 h / Heating

12.1: 75 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

13.1: 77 percent / DDQ / CH₂Cl₂ / Heating

14.1: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

15.1: 73 percent / TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 14 h / 20 °C

16.1: 16 percent / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 20 h / 0 - 20 °C

17.1: Kirsching's resin; TEMPO / CH₂Cl₂ / 2 h / 20 °C

18.1: I₂; KOH / 0.75 h / 0 - 20 °C

With 1H-imidazole; aluminum oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); dibromodifluoromethane; Kirsching's resin; borane; iodine; tri-n-butyl-tin hydride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 4.1: Ramberg-Baeclund reaction;

DOI:10.1021/jo034607k

Reference yield:

(4aR,6S,7R,8R,8aS)-6-Benzylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol → (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate (623148-81-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 86 percent / NaH; TBAI / dimethylformamide; tetrahydrofuran / 0 - 20 °C

2.1: 95 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; ethanol; H₂O / 3 h / 65 °C

3.1: 70 percent / KOH/alumina; CF₂Br₂ / 2-methyl-propan-2-ol; CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: borane / tetrahydrofuran / 3 h / 0 - 20 °C

4.2: 53 percent / KOH; H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

5.1: 98 percent / iPr₂NEt / CH₂Cl₂ / 10 h / 20 °C

6.1: 85 percent / DDQ / CH₂Cl₂ / 1.5 h / 20 °C

7.1: NaH / dimethylformamide / 0.25 h / 0 °C

7.2: 77 percent / N-tosylimidazole / dimethylformamide / 1.25 h / 0 - 20 °C

8.1: 100 percent / methanol / 20 h / 120 °C

9.1: 100 percent / p-TsOH*H₂O / methanol / 20 °C

10.1: 85 percent / imidazole; PPh₃; I₂ / tetrahydrofuran / 2 h / Heating

11.1: 75 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

12.1: 77 percent / DDQ / CH₂Cl₂ / Heating

13.1: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

14.1: 73 percent / TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 14 h / 20 °C

15.1: 16 percent / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 20 h / 0 - 20 °C

16.1: Kirsching's resin; TEMPO / CH₂Cl₂ / 2 h / 20 °C

17.1: I₂; KOH / 0.75 h / 0 - 20 °C

With 1H-imidazole; aluminum oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); dibromodifluoromethane; Kirsching's resin; borane; iodine; tri-n-butyl-tin hydride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 3.1: Ramberg-Baeclund reaction;

DOI:10.1021/jo034607k

Reference yield:

(1R)-2,6-anhydro-1-phenyl-1-O-[2-(trimethylsilyl)ethoxymethyl]-3,4-anhydro-5,7-O-benzylidene-α-D-manno-heptitol → (2S)-methyl 3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octitolate (623148-81-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / methanol / 20 h / 120 °C

2: 100 percent / p-TsOH*H₂O / methanol / 20 °C

3: 85 percent / imidazole; PPh₃; I₂ / tetrahydrofuran / 2 h / Heating

4: 75 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

5: 77 percent / DDQ / CH₂Cl₂ / Heating

6: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

7: 73 percent / TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 14 h / 20 °C

8: 16 percent / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 20 h / 0 - 20 °C

9: Kirsching's resin; TEMPO / CH₂Cl₂ / 2 h / 20 °C

10: I₂; KOH / 0.75 h / 0 - 20 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); Kirsching's resin; iodine; tri-n-butyl-tin hydride; titanium tetrachloride; toluene-4-sulfonic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jo034607k

upstream raw materials:

methanol

(2S)-3,7-anhydro-2-phenyl-4,6-bis-O-tert-butyldimethylsilyl-5-O-methyl-8-deoxy-α-D-altro-octital

benzyl 1-thio-β-D-glucopyranoside

2,6-anhydro-1-phenyl-1-keto-4-O-methyl-7-deoxy-α-D-altro-heptitol

Downstream raw materials:

(2S)-methyl 3,7-anhydro-2-phenyl-5-O-methyl-8-deoxy-α-D-altro-octitolate

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