(2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester
CAS No.:99285-10-6
Molecular Formula:C₃₆H₅₀O₁₀
Molecular Weight:642.787
Hs Code.:

(2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

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Chemical Property of (2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

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Technology Process of (2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

There total 10 articles about (2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-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: 82.0%

: 99285-06-0,99340-62-2
(2R,3S,4S)-4-((2R,3R,5R,6R,8S,9R,10S,11S)-3-Benzyloxy-8-ethyl-9,10-dihydroxy-3,5,9,11-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

: 1885-14-9
phenyl chloroformate

: 99285-10-6,99340-65-5
(2R,3S,4S)-4-((2R,3R,5R,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1139/v85-470

Reference yield: 82.0%

: 99285-06-0,99340-62-2
(2R,3S,4S)-4-((2R,3R,5S,6R,8S,9R,10S,11S)-3-Benzyloxy-8-ethyl-9,10-dihydroxy-3,5,9,11-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

: 1885-14-9
phenyl chloroformate

: 99285-10-6,99340-65-5
(2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

Guidance literature:: With pyridine; In dichloromethane; benzene; at 0 ℃; for 0.5h;
DOI:10.1139/v85-469

Reference yield:

: 100-39-0
benzyl bromide

: 99285-10-6,99340-65-5
(2R,3S,4S)-4-((2R,3R,5S,6R,8S,9S,10S,11S)-3-Benzyloxy-8-ethyl-9-hydroxy-3,5,9,11-tetramethyl-10-phenoxycarbonyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / NaH / dimethylformamide / 2.5 h / 25 °C

2: 71 percent / acetyl chloride / methanol / 1.5 h / 25 °C

3: 95 percent / HCl, Drierite / 1 h / 0 °C

4: 60 percent / pyridinium chlorochromate, molecular sieve 3 Angstroem, / CH₂Cl₂ / 2.5 h / 25 °C

5: 100 percent / 80percent acetic acid / CH₂Cl₂

6: sodium acetate / methanol / 5 h / 25 °C

7: 80percent acetic acid / CH₂Cl₂ / 5 h / 30 °C

8: 82 percent / pyridine / benzene; CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; hydrogenchloride; calcium sulfate; 3 A molecular sieve; sodium acetate; sodium hydride; acetic acid; acetyl chloride; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1139/v85-469