(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester
CAS No.:94059-76-4
Molecular Formula:C₂₆H₃₈O₇
Molecular Weight:462.584
Hs Code.:

Synonyms:(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

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Chemical Property of (2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

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Technology Process of (2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

There total 8 articles about (2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl 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: 77.0%

: 108-24-7
acetic anhydride

: 94059-75-3,94425-19-1
(2R,3S,4S)-4-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

: 94059-76-4
(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

Guidance literature:: With dmap; In triethylamine; for 3h; Ambient temperature;
DOI:10.1139/v84-496

Reference yield:

: 94059-70-8
(2R,3R,6S)-2-((S)-2-Hydroxy-1-methyl-ethyl)-3-methyl-1,7-dioxa-spiro[5.5]undecan-3-ol

: 94059-76-4
(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 69 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4.5 h

2: 68 percent / 50 percent NaH in oil / dimethylformamide / 2 h / 55 °C

3: 63 percent / H₂O, 1 N HCl / 1,2-dimethoxy-ethane / r.t., 1 h then 50 deg C, 45 min

4: 94 percent / pyridinium chlorochromate, molecular sieves (3 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

5: 1.) n-BuLi/hexane, diisopropylamine/THF, methyl propionate, bis(cyclopentadienyl) zirconium dichloride / 1.) -78 deg C, 10 min; -40 deg C, 10 min then r.t., 30 min; 2.) THF, -78 deg C, 2 h then -50 deg C, 1 h

6: 77 percent / 4-dimethylamino pyridine / triethylamine / 3 h / Ambient temperature

With tetrahydrofuran; hydrogenchloride; dmap; n-butyllithium; zirconocene dichloride; hexane; propanoic acid methyl ester; 3 A molecular sieve; water; pyridinium p-toluenesulfonate; sodium hydride; diisopropylamine; pyridinium chlorochromate; In 1,2-dimethoxyethane; dichloromethane; triethylamine; N,N-dimethyl-formamide;
DOI:10.1139/v84-496

Reference yield:

: 94059-71-9
(2R,3R,6S)-3-Methyl-2-[(S)-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,7-dioxa-spiro[5.5]undecan-3-ol

: 94059-76-4
(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 68 percent / 50 percent NaH in oil / dimethylformamide / 2 h / 55 °C

2: 63 percent / H₂O, 1 N HCl / 1,2-dimethoxy-ethane / r.t., 1 h then 50 deg C, 45 min

3: 94 percent / pyridinium chlorochromate, molecular sieves (3 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) n-BuLi/hexane, diisopropylamine/THF, methyl propionate, bis(cyclopentadienyl) zirconium dichloride / 1.) -78 deg C, 10 min; -40 deg C, 10 min then r.t., 30 min; 2.) THF, -78 deg C, 2 h then -50 deg C, 1 h

5: 77 percent / 4-dimethylamino pyridine / triethylamine / 3 h / Ambient temperature

With tetrahydrofuran; hydrogenchloride; dmap; n-butyllithium; zirconocene dichloride; hexane; propanoic acid methyl ester; 3 A molecular sieve; water; sodium hydride; diisopropylamine; pyridinium chlorochromate; In 1,2-dimethoxyethane; dichloromethane; triethylamine; N,N-dimethyl-formamide;
DOI:10.1139/v84-496