(S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

Base Information

• Chemical Name: (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one
• CAS No.: 128271-03-4
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 128271-03-4.mol

Synonyms:(S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

Chemical Property of (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

There total 45 articles about (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one 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:

(2Ξ,3R)-4,4-Dimethyl-tetrahydro-furan-2,3-diol (103203-99-2,133094-80-1,133094-96-9,134932-06-2,134932-07-3) → (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one (128271-03-4)

Guidance literature:

Multi-step reaction with 24 steps

1: CSA

2: NaH

3: AcOH / H₂O

4: 1.) PivCl, 2.) MsCl, 3.) K₂CO₃ / 1.) pyridine, 2.) pyridine, 3.) MeOH

5: 99 percent / CuI / tetrahydrofuran / -23 deg C to room temperature

6: 1.) OsO₄, NMO, 2.) NaIO₄ / 1.) aq. acetone, t-BuOH, room temperature, 2.) aq. THF, room temperature

7: 67 percent / MsCl, Et₃N, i-Pr₂NEt / CH₂Cl₂ / Heating

8: CH₂Cl₂ / Ambient temperature

9: LiAlH₄ / tetrahydrofuran / Heating

10: 92 percent / imidazole / dimethylformamide / Ambient temperature

11: 90 percent / CSA / CH₂Cl₂ / Ambient temperature

12: 85 percent / H₂ / Pd(OH)2 / tetrahydrofuran / Ambient temperature

13: 92 percent / (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 deg C to room temperature

14: tetrahydrofuran / 0 °C

15: AcOH / H₂O / 60 °C

16: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, -78 deg C to room temperature

17: CSA / methanol / Ambient temperature

18: CSA / CH₂Cl₂ / Ambient temperature

19: 1.) PDC, 2.) n-Bu₄NF / 1.) CH₂Cl₂, room temeperature, 2.) THF, room temperature

20: NaBH₄, CeCl₃ / methanol / -78 deg C - to room temperature

21: KH / tetrahydrofuran / 0 °C

22: 81 percent / m-CPBA / Ambient temperature

23: NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

24: 1.) p-TsOH / 1.) MeOH, 2.) benzene

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; N-methyl-2-indolinone; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pivaloyl chloride; potassium hydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)88289-4

Reference yield:

(R)-4-benzyloxy-3,3-dimethyl-butane-1,2-diol (104708-09-0) → (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one (128271-03-4)

Guidance literature:

Multi-step reaction with 21 steps

1: 1.) PivCl, 2.) MsCl, 3.) K₂CO₃ / 1.) pyridine, 2.) pyridine, 3.) MeOH

2: 99 percent / CuI / tetrahydrofuran / -23 deg C to room temperature

3: 1.) OsO₄, NMO, 2.) NaIO₄ / 1.) aq. acetone, t-BuOH, room temperature, 2.) aq. THF, room temperature

4: 67 percent / MsCl, Et₃N, i-Pr₂NEt / CH₂Cl₂ / Heating

5: CH₂Cl₂ / Ambient temperature

6: LiAlH₄ / tetrahydrofuran / Heating

7: 92 percent / imidazole / dimethylformamide / Ambient temperature

8: 90 percent / CSA / CH₂Cl₂ / Ambient temperature

9: 85 percent / H₂ / Pd(OH)2 / tetrahydrofuran / Ambient temperature

10: 92 percent / (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 deg C to room temperature

11: tetrahydrofuran / 0 °C

12: AcOH / H₂O / 60 °C

13: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, -78 deg C to room temperature

14: CSA / methanol / Ambient temperature

15: CSA / CH₂Cl₂ / Ambient temperature

16: 1.) PDC, 2.) n-Bu₄NF / 1.) CH₂Cl₂, room temeperature, 2.) THF, room temperature

17: NaBH₄, CeCl₃ / methanol / -78 deg C - to room temperature

18: KH / tetrahydrofuran / 0 °C

19: 81 percent / m-CPBA / Ambient temperature

20: NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

21: 1.) p-TsOH / 1.) MeOH, 2.) benzene

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; N-methyl-2-indolinone; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pivaloyl chloride; potassium hydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)88289-4

Reference yield:

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane (111080-21-8) → (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one (128271-03-4)

Guidance literature:

Multi-step reaction with 20 steps

1: 99 percent / CuI / tetrahydrofuran / -23 deg C to room temperature

2: 1.) OsO₄, NMO, 2.) NaIO₄ / 1.) aq. acetone, t-BuOH, room temperature, 2.) aq. THF, room temperature

3: 67 percent / MsCl, Et₃N, i-Pr₂NEt / CH₂Cl₂ / Heating

4: CH₂Cl₂ / Ambient temperature

5: LiAlH₄ / tetrahydrofuran / Heating

6: 92 percent / imidazole / dimethylformamide / Ambient temperature

7: 90 percent / CSA / CH₂Cl₂ / Ambient temperature

8: 85 percent / H₂ / Pd(OH)2 / tetrahydrofuran / Ambient temperature

9: 92 percent / (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 deg C to room temperature

10: tetrahydrofuran / 0 °C

11: AcOH / H₂O / 60 °C

12: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, -78 deg C to room temperature

13: CSA / methanol / Ambient temperature

14: CSA / CH₂Cl₂ / Ambient temperature

15: 1.) PDC, 2.) n-Bu₄NF / 1.) CH₂Cl₂, room temeperature, 2.) THF, room temperature

16: NaBH₄, CeCl₃ / methanol / -78 deg C - to room temperature

17: KH / tetrahydrofuran / 0 °C

18: 81 percent / m-CPBA / Ambient temperature

19: NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

20: 1.) p-TsOH / 1.) MeOH, 2.) benzene

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; N-methyl-2-indolinone; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)88289-4

upstream raw materials:

((2S,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-methanol

(2R,4S,5R,6S)-2-Allyl-5-benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran

(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

benzyl bromide

Downstream raw materials:

(2R,4S,5R,6S)-2-Allyl-5-benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran

(S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

mycalamide A

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4R,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide