Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester

Base Information

• Chemical Name: Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester
• CAS No.: 312487-65-3
• Molecular Formula: C₂₉H₃₉ClO₈S
• Molecular Weight: 583.143

Synonyms:

Chemical Property of Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester

There total 15 articles about Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester 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:

(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol (174198-73-3) → Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester (312487-65-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

2: imidazole / dimethylformamide / 25 °C

3: K₂CO₃ / methanol / 25 °C

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

5: LDA / tetrahydrofuran / -78 °C

6: TBAF / tetrahydrofuran / 25 °C

7: LiOH / H₂O; tetrahydrofuran / 0 °C

8: pyridine / 25 °C

9: 88 percent / DBU / benzene / 25 °C

10: 89 percent / diethyl ether / 0 °C

11: LiAlH₄ / diethyl ether / 0 - 25 °C

12: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

13: CSA / methanol / 25 °C

14: 2,4,6-collidine / CH₂Cl₂ / -78 °C

15: 2,6-lutidine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; lithium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS-4 Angstroem; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Acetylation / 2: silylation / 3: Hydrolysis / 4: Oxidation / 5: Addition / 6: ether cleavage / 7: Hydrolysis / 8: Cyclization / 9: Elimination / 10: Addition / 11: Reduction / 12: Alkylation / 13: Hydrolysis / 14: Acetylation / 15: Acylation;

DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

(4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-2-one (312487-61-9) → Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester (312487-65-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / diethyl ether / 0 °C

2: LiAlH₄ / diethyl ether / 0 - 25 °C

3: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

4: CSA / methanol / 25 °C

5: 2,4,6-collidine / CH₂Cl₂ / -78 °C

6: 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Addition / 2: Reduction / 3: Alkylation / 4: Hydrolysis / 5: Acetylation / 6: Acylation;

DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

Acetic acid (2R,3S,6S)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl ester → Acetic acid (R)-2-[(2S,5S,6R)-5-benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-methyl-tetrahydro-pyran-2-yl]-2-chloromethanesulfonyloxy-ethyl ester (312487-65-3)

Guidance literature:

Multi-step reaction with 14 steps

1: imidazole / dimethylformamide / 25 °C

2: K₂CO₃ / methanol / 25 °C

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

4: LDA / tetrahydrofuran / -78 °C

5: TBAF / tetrahydrofuran / 25 °C

6: LiOH / H₂O; tetrahydrofuran / 0 °C

7: pyridine / 25 °C

8: 88 percent / DBU / benzene / 25 °C

9: 89 percent / diethyl ether / 0 °C

10: LiAlH₄ / diethyl ether / 0 - 25 °C

11: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

12: CSA / methanol / 25 °C

13: 2,4,6-collidine / CH₂Cl₂ / -78 °C

14: 2,6-lutidine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; lithium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS-4 Angstroem; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: silylation / 2: Hydrolysis / 3: Oxidation / 4: Addition / 5: ether cleavage / 6: Hydrolysis / 7: Cyclization / 8: Elimination / 9: Addition / 10: Reduction / 11: Alkylation / 12: Hydrolysis / 13: Acetylation / 14: Acylation;

DOI:10.1016/S0040-4039(00)01340-X

upstream raw materials:

monochloromethanesulfonyl chloride

(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol

(4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-2-one

(4R,4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,6-dimethyl-hexahydro-pyrano[3,2-b]pyran-2-one

Downstream raw materials:

{(2R,3R)-3-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-ylmethyl]-2-methyl-oxiranyl}-methanol

2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol

{(2S,3R,6S,7R)-6-Benzyloxy-7-((R)-3-benzyloxy-1-methyl-propyl)-3-methyl-2-[(2R,3R)-3-methyl-3-((E)-styryl)-oxiranylmethyl]-oxepan-3-yloxy}-trimethyl-silane

(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-((2R,3R)-3-hydroxymethyl-3-methyl-oxiranylmethyl)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-3-ol

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