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【结 构 式】 
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【分子编号】20194 【品名】1(S)-[5(R)-[5(R)-[1(R)-Hydroxy-2-(p-toluenesulfonyloxy)ethyl]tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]undecan-1-ol 【CA登记号】 |
【 分 子 式 】C28H46O7S 【 分 子 量 】526.73504 【元素组成】C 63.85% H 8.8% O 21.26% S 6.09% |
合成路线1
该中间体在本合成路线中的序号：(XIX)2) The reduction of (XIV) with DIBAL followed by protection with methoxymethyl chloride (MOM-Cl) yields the methoxymethyl ether (XV), which by regioselective dihydroxylation with AD-mix-beta, followed by mesylation with mesyl chloride affords the dimesylate (XVI). A new regioselective dihydroxylation of (XVI) with AD-mix-beta gives the diol (XVII), which is cyclized by treatment first with p-toluenesulfonic acid and then by heating at 140 C in pyridine yielding the bis(tetrahydrofuran) derivative (XVIII). The deprotection of (XVIII) with boron trilfuoride.ethearate, followed by tosylation with tosyl chloride in pyridine affords the tosylate (XIX), which is cyclized to the epoxide (XX) by reaction with K2CO3 in methanol. The acetylation of the secondary alcohol of (XIX) with acetic anhydride in pyridine affords the acetate (XXI), which is condensed with trimethylsilylacetylene (XXII) by means of n-BuLi in THF giving the acetylenic alcohol (XXIII).
| 【1】 Yazbak, A.; et al.; Total synthesis of uvaricin. J Org Chem 1998, 63, 17, 5863. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 20188 | ethyl (2E,6E)-9-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,6-nonadienoate | C26H46O4 | 详情 | 详情 | |
| (XV) | 20190 | (2E,6E)-9-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,6-nonadienyl methoxymethyl ether; (4S,5R)-4-decyl-5-[(3E,7E)-9-(methoxymethoxy)-3,7-nonadienyl]-2,2-dimethyl-1,3-dioxolane | C26H48O4 | 详情 | 详情 | |
| (XVI) | 20191 | (4S,5R)-4-decyl-5-((3S,4S,7E)-9-(methoxymethoxy)-3,4-bis[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-7-nonenyl)-2,2-dimethyl-1,3-dioxolane; (E,6S,7S)-9-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]-6,7-bis[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2-nonenyl methoxymethyl ether | C32H62O6S2 | 详情 | 详情 | |
| (XVII) | 20192 | (4S,5S,8R,9R)-4-[2-[(4R,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-2-methyl-5-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2-methylene-3,11,13-trioxa-2lambda(6)-thia-1-tetradecene-8,9-diol | C32H64O8S2 | 详情 | 详情 | |
| (XVIII) | 20193 | 1(S)-[5(R)-[5(R)-[1(R)-Hydroxy-2-(methoxymethoxy)ethyl]tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]undecan-1-ol | C23H44O6 | 详情 | 详情 | |
| (XIX) | 20194 | 1(S)-[5(R)-[5(R)-[1(R)-Hydroxy-2-(p-toluenesulfonyloxy)ethyl]tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]undecan-1-ol | C28H46O7S | 详情 | 详情 | |
| (XX) | 20195 | 1(S)-[5(R)-[5(R)-(1(R),2-Epoxyethyl)tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]undecan-1-ol | C21H38O4 | 详情 | 详情 | |
| (XXI) | 20196 | Acetic acid 1(S)-[5(R)-[5(R)-(1(R),2-Epoxyethyl)tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]undecyl ester | C23H40O5 | 详情 | 详情 | |
| (XXII) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (XXIII) | 20198 | Acetic acid 1(S)-[5(R)-[5(R)-(1(R)-hydoxy-3-butynyl)tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]undecyl ester | C25H42O5 | 详情 | 详情 | |
| (XXIV) | 20205 | (5S)-3-[(E)-9-iodo-8-nonenyl]-5-methyl-3-(phenylsulfanyl)dihydro-2(3H)-furanone | C20H27IO2S | 详情 | 详情 |