(R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol

Base Information

• Chemical Name: (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol
• CAS No.: 312493-80-4
• Molecular Formula: C₃₄H₄₈O₅Si
• Molecular Weight: 564.838

Synonyms:(R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol

Chemical Property of (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol

There total 17 articles about (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol 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:

(4aS,6R,7S,8aR)-6-Hydroxymethyl-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (312308-12-6) → (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol (312493-80-4)

Guidance literature:

Multi-step reaction with 17 steps

1: 2,6-lutidine / CH₂Cl₂ / -78 °C

2: 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

3: n-BuLi / tetrahydrofuran; various solvent(s) / -20 °C

4: PPTS / methanol / 0 °C

5: 88 percent / Red-Al / diethyl ether / 25 °C

6: 93 percent / t-BuOOH; (+)-DET; Ti(i-PrO)4, MS-4 Angstroem / CH₂Cl₂ / -20 °C

7: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

8: NaHMDS / tetrahydrofuran / 0 °C

9: TBAF / tetrahydrofuran / 25 °C

10: NaH / dimethylsulfoxide / 0 - 25 °C

11: 96 percent / n-Bu₄NBr; NaH / tetrahydrofuran / 0 - 25 °C

12: 94 percent / CSA / methanol / 25 °C

13: 2,4,6-collidine / CH₂Cl₂ / -78 °C

14: 2,6-lutidine / CH₂Cl₂ / 0 °C

15: K₂CO₃ / methanol / 25 °C

16: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

17: tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; MS-4 Angstroem; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 1: Acylation / 2: silylation / 3: Substitution / 4: Hydrolysis / 5: Hydrogenation / 6: Epoxidation / 7: Oxidation / 8: Condensation / 9: ether cleavage / 10: Cyclization / 11: Alkylation / 12: Hydrolysis / 13: Acetylation / 14: silylation / 15: Hydrolysis / 16: Oxidation / 17: Grignard reaction;

DOI:10.1016/S0040-4039(00)01339-3

Reference yield:

(4aS,6R,7S,8aR)-2,2,4a-Trimethyl-6-[(2S,3S)-3-((E)-styryl)-oxiranylmethyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol → (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol (312493-80-4)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / dimethylsulfoxide / 0 - 25 °C

2: 96 percent / n-Bu₄NBr; NaH / tetrahydrofuran / 0 - 25 °C

3: 94 percent / CSA / methanol / 25 °C

4: 2,4,6-collidine / CH₂Cl₂ / -78 °C

5: 2,6-lutidine / CH₂Cl₂ / 0 °C

6: K₂CO₃ / methanol / 25 °C

7: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

8: tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS-4 Angstroem; tetrabutylammomium bromide; sodium hydride; potassium carbonate; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1: Cyclization / 2: Alkylation / 3: Hydrolysis / 4: Acetylation / 5: silylation / 6: Hydrolysis / 7: Oxidation / 8: Grignard reaction;

DOI:10.1016/S0040-4039(00)01339-3

Reference yield:

Trifluoro-methanesulfonic acid (4aS,6R,7S,8aR)-7-hydroxy-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl ester → (R)-1-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-but-3-en-1-ol (312493-80-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

2: n-BuLi / tetrahydrofuran; various solvent(s) / -20 °C

3: PPTS / methanol / 0 °C

4: 88 percent / Red-Al / diethyl ether / 25 °C

5: 93 percent / t-BuOOH; (+)-DET; Ti(i-PrO)4, MS-4 Angstroem / CH₂Cl₂ / -20 °C

6: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

7: NaHMDS / tetrahydrofuran / 0 °C

8: TBAF / tetrahydrofuran / 25 °C

9: NaH / dimethylsulfoxide / 0 - 25 °C

10: 96 percent / n-Bu₄NBr; NaH / tetrahydrofuran / 0 - 25 °C

11: 94 percent / CSA / methanol / 25 °C

12: 2,4,6-collidine / CH₂Cl₂ / -78 °C

13: 2,6-lutidine / CH₂Cl₂ / 0 °C

14: K₂CO₃ / methanol / 25 °C

15: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

16: tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; MS-4 Angstroem; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 1: silylation / 2: Substitution / 3: Hydrolysis / 4: Hydrogenation / 5: Epoxidation / 6: Oxidation / 7: Condensation / 8: ether cleavage / 9: Cyclization / 10: Alkylation / 11: Hydrolysis / 12: Acetylation / 13: silylation / 14: Hydrolysis / 15: Oxidation / 16: Grignard reaction;

DOI:10.1016/S0040-4039(00)01339-3

upstream raw materials:

allylmagnesium bromide

(4aS,6R,7S,8aR)-6-Hydroxymethyl-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(4aS,6S,7R,8aS,9aR,10aR)-2,2,4a-Trimethyl-7-((E)-styryl)-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

(E)-4-[(4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-but-2-en-1-ol

Downstream raw materials:

(4R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-methoxy-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

(R)-4-[(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-3-hydroxy-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-2-yl]-butane-1,2,4-triol

(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-2-((R)-1-hydroxy-but-3-enyl)-2-methyl-6-((E)-styryl)-octahydro-pyrano[3,2-b]pyran-3-ol

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