(S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one

Base Information

• Chemical Name: (S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one
• CAS No.: 168072-74-0
• Molecular Formula: C₃₀H₄₂O₈Si
• Molecular Weight: 558.744
• Mol file: 168072-74-0.mol

Synonyms:(S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one

Chemical Property of (S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-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,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one

There total 15 articles about (S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-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: 87.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (S)-4-[(2R,4S,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl]-[1,3]dioxolan-2-one → (S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one (168072-74-0)

Guidance literature:

With 1H-imidazole; In toluene; at 23 ℃;

DOI:10.1016/0040-4039(95)00093-R

Reference yield:

(S)-1-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-but-3-en-1-ol (152998-13-5) → (S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one (168072-74-0)

Guidance literature:

Multi-step reaction with 15 steps

1: dimethylformamide / 23 °C

2: 1) ozone, 2) PPh₃ / 1) -78 deg C

3: TiCl₄

4: 1) BuLi / 1) THF, 0 deg C, 2) 23 deg C

5: 1) IBr, 2) NaOH (sat.) / 1) CH₂Cl₂, -78 deg C, 2) dioxane, H₂O, 23 deg C

6: NaOAc, H₂O / dimethylformamide / 65 °C

7: pyridine / CH₂Cl₂ / -78 °C

8: pyridine / CH₂Cl₂ / 0 °C

9: H₂O, AcOH / 80 °C

10: KIO₄ / tetrahydrofuran; H₂O

11: 93 percent / 4A mol sieves / toluene / -78 °C

12: 1) dimethyldioxirane, 2) AcOH / 1) acetone, 2) MeOH, 23 deg C

13: Ti(O-i-Pr)4, (-)-DIPT, TBHP / CH₂Cl₂ / -20 °C

14: Zn, AcOH / 50 °C

15: 87 percent / imidazol / toluene / 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; potassium metaperiodate; 4 A molecular sieve; water; sodium acetate; 3,3-dimethyldioxirane; iodine(I) bromide; titanium tetrachloride; D-(-)-diisopropyl tartrate; ozone; acetic acid; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(95)00093-R

Reference yield:

(R)-2,2-Diethyl-4-((S)-1-methoxy-2,2-dimethyl-but-3-enyl)-[1,3]dioxolane (152998-14-6) → (S)-4-{(2R,4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-5-hydroxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-[1,3]dioxolan-2-one (168072-74-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 1) ozone, 2) PPh₃ / 1) -78 deg C

2: TiCl₄

3: 1) BuLi / 1) THF, 0 deg C, 2) 23 deg C

4: 1) IBr, 2) NaOH (sat.) / 1) CH₂Cl₂, -78 deg C, 2) dioxane, H₂O, 23 deg C

5: NaOAc, H₂O / dimethylformamide / 65 °C

6: pyridine / CH₂Cl₂ / -78 °C

7: pyridine / CH₂Cl₂ / 0 °C

8: H₂O, AcOH / 80 °C

9: KIO₄ / tetrahydrofuran; H₂O

10: 93 percent / 4A mol sieves / toluene / -78 °C

11: 1) dimethyldioxirane, 2) AcOH / 1) acetone, 2) MeOH, 23 deg C

12: Ti(O-i-Pr)4, (-)-DIPT, TBHP / CH₂Cl₂ / -20 °C

13: Zn, AcOH / 50 °C

14: 87 percent / imidazol / toluene / 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; potassium metaperiodate; 4 A molecular sieve; water; sodium acetate; 3,3-dimethyldioxirane; iodine(I) bromide; titanium tetrachloride; D-(-)-diisopropyl tartrate; ozone; acetic acid; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(95)00093-R

upstream raw materials:

tert-butylchlorodiphenylsilane

(S)-1-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-but-3-en-1-ol

(R)-2,2-Diethyl-4-((S)-1-methoxy-2,2-dimethyl-but-3-enyl)-[1,3]dioxolane

(S)-3-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-3-methoxy-2,2-dimethyl-propionaldehyde

Downstream raw materials:

(S)-4-[(4R,4aR,6R,8S,8aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-[1,3]dioxolan-2-one

N-[(4S,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]-benzamide