(4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione

Base Information

• Chemical Name: (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione
• CAS No.: 138723-31-6
• Molecular Formula: C₂₇H₄₂O₆SSi
• Molecular Weight: 522.778
• Mol file: 138723-31-6.mol

Synonyms:

Chemical Property of (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione

There total 8 articles about (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione 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:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione (138723-31-6,138810-11-4)

Guidance literature:

Multi-step reaction with 8 steps

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂

3: H₂, HClO₄ / Pd/C / methanol

4: pyridine

5: pyridine / DMAP / CH₂Cl₂

6: 1) nBu₂SnO, 2) Br₂ / 1) PhCH₃, 2) CCl₄

7: 82 percent / tetrahydrofuran

8: NaH, nBu₄NI, CH₃I

With pyridine; triethylsilane; perchloric acid; boron trifluoride diethyl etherate; hydrogen; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; methyl iodide; dmap; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00030a005

Reference yield:

(2S,3R,4R,5S,6R)-2-(4-Hydroxy-3,3-dimethyl-butyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (138723-42-9) → (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione (138723-31-6,138810-11-4)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

2: pyridine / DMAP / CH₂Cl₂

3: 1) nBu₂SnO, 2) Br₂ / 1) PhCH₃, 2) CCl₄

4: 82 percent / tetrahydrofuran

5: NaH, nBu₄NI, CH₃I

With pyridine; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; methyl iodide; dmap; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00030a005

Reference yield:

C19H21LiOSi (138723-27-0) → (4S,5aR,8R,9aR,9bS)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyl]-3a-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine-2-thione (138723-31-6,138810-11-4)

Guidance literature:

Multi-step reaction with 8 steps

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂

3: H₂, HClO₄ / Pd/C / methanol

4: pyridine

5: pyridine / DMAP / CH₂Cl₂

6: 1) nBu₂SnO, 2) Br₂ / 1) PhCH₃, 2) CCl₄

7: 82 percent / tetrahydrofuran

8: NaH, nBu₄NI, CH₃I

With pyridine; triethylsilane; perchloric acid; boron trifluoride diethyl etherate; hydrogen; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; methyl iodide; dmap; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00030a005

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4R,5S,6R)-2-(4-Hydroxy-3,3-dimethyl-butyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

C₁₉H₂₁LiOSi

(2R,4aR,6S,7R,8R,8aS)-6-(4-Hydroxy-3,3-dimethyl-butyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde

(2R,4aR,6S,8aS)-6-((Z)-3,3-Dimethyl-hepta-4,6-dienyl)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

tert-Butyl-[2,2-dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butoxy]-dimethyl-silane