(2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol

Base Information

• Chemical Name: (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol
• CAS No.: 204448-29-3
• Molecular Formula: C₃₇H₆₀O₇S₂
• Molecular Weight: 681.011

Synonyms:(2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol

Chemical Property of (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol

Chemical Property:

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Technology Process of (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol

There total 20 articles about (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol 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:

(2S,4S,7R)-1-{2-[(2S,4S)-6-Benzyloxy-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-hexyl]-[1,3]dithian-2-yl}-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol (204448-54-4) → (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol (204448-29-3)

Guidance literature:

With tetrabutyl ammonium fluoride; at 0 ℃; Yield given;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<187::aid-anie187>3.0.co;2-d

Reference yield:

(R)-1-benzyloxy-hex-5-en-3-ol (111322-01-1,119239-98-4,91285-62-0) → (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol (204448-29-3)

Guidance literature:

Multi-step reaction with 9 steps

2: 92 percent / imidazole / CH₂Cl₂

3: 97 percent / BuLi, DMPU / tetrahydrofuran / 1.) -20 deg C; -78 deg C, 2.) -20 deg C

4: 87 percent / imidazole / CH₂Cl₂

5: 59 percent / tert-BuONa, BuLi / pentane / 1.) -78 deg C, 2.) -78 to -20 deg C

6: 80 percent / PPTS, MeOH

7: 93 percent / NaH, p-toluenesulfonyl imidazole / tetrahydrofuran / 1.) 0 deg C, 2.) 0 deg C

8: 1.) tert-BuLi, 2.) lithium 2-thienylcyanocuprate / 1.) THF, -78 deg C, 2.) -78 to 0 deg C

9: TBAF / 0 °C

With 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; thien-2-yl(cyano)copper lithium; N-tosylimidazole; sodium t-butanolate; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<187::aid-anie187>3.0.co;2-d

Reference yield:

(S)-(2-phenylmethoxyethyl)oxirane (85960-55-0) → (2S,4S,7R)-1-[2-((2S,4S)-6-Benzyloxy-2,4-dihydroxy-hexyl)-[1,3]dithian-2-yl]-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol (204448-29-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) CuCN / 1.) -78 deg C, 2.) -30 to 0 deg C

3: 92 percent / imidazole / CH₂Cl₂

4: 97 percent / BuLi, DMPU / tetrahydrofuran / 1.) -20 deg C; -78 deg C, 2.) -20 deg C

5: 87 percent / imidazole / CH₂Cl₂

6: 59 percent / tert-BuONa, BuLi / pentane / 1.) -78 deg C, 2.) -78 to -20 deg C

7: 80 percent / PPTS, MeOH

8: 93 percent / NaH, p-toluenesulfonyl imidazole / tetrahydrofuran / 1.) 0 deg C, 2.) 0 deg C

9: 1.) tert-BuLi, 2.) lithium 2-thienylcyanocuprate / 1.) THF, -78 deg C, 2.) -78 to 0 deg C

10: TBAF / 0 °C

With 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; thien-2-yl(cyano)copper lithium; N-tosylimidazole; sodium t-butanolate; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<187::aid-anie187>3.0.co;2-d

upstream raw materials:

(2S,4S,7R)-1-{2-[(2S,4S)-6-Benzyloxy-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-hexyl]-[1,3]dithian-2-yl}-2-methyl-7-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-6-methylene-octane-2,4-diol

cycloxexanone dimethyl ketal

(R)-1-benzyloxy-hex-5-en-3-ol

(S)-(2-phenylmethoxyethyl)oxirane

Downstream raw materials:

(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-2-[(R)-3-((2S,3R)-3-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-2-methylene-butyl]-1,7-dioxa-spiro[5.5]undecane-4,10-diol

C₅₂H₈₂O₁₇Si

C₅₈H₉₈O₁₆Si₂

C₅₉H₉₀O₁₅Si₂

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