(4S,5R)-5-[(3aR,4R,6R,7aR)-6-[(1S,2R,6R)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylidene-1-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde | 920018-95-7

分子结构分类

有机化合物 - 有机杂环化合物 - 二氧吡喃

中文名称

——

中文别名

——

英文名称

(4S,5R)-5-[(3aR,4R,6R,7aR)-6-[(1S,2R,6R)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylidene-1-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

英文别名

——

(4S,5R)-5-[(3aR,4R,6R,7aR)-6-[(1S,2R,6R)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylidene-1-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde化学式

CAS

920018-95-7

化学式

C₅₉H₁₁₂O₁₆Si₄

mdl

——

分子量

1189.87

InChiKey

HMKDWUABTYBHIF-HXZIHLDFSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

12.42
重原子数：

79
可旋转键数：

26
环数：

6.0
sp3杂化的碳原子比例：

0.95
拓扑面积：

156
氢给体数：

0
氢受体数：

16

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	[(4R,5S)-5-[(3aR,4R,6R,7aR)-6-[(1R,5R,6S)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methylidene-6-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy-tert-butyl-dimethylsilane	920018-89-9	C₆₆H₁₂₀O₁₆Si₄	1282.01
——	[(1R)-1-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-4-trimethylstannylpent-4-enoxy]-tert-butyl-dimethylsilane	920018-87-7	C₃₄H₆₈O₇Si₂Sn	763.791
——	(2S)-2-[(3aR,4R,6R,7aR)-4-[(4S,5R)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2-(2-trimethylsilylethoxymethoxy)acetaldehyde	920018-88-8	C₂₉H₄₆O₉Si	566.764

反应信息

作为反应物：

描述：

[(4E,6E,8E,12E)-pentadeca-4,6,8,12,14-pentaenyl]sulfonylbenzene 、 (4S,5R)-5-[(3aR,4R,6R,7aR)-6-[(1S,2R,6R)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylidene-1-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 在 lithium diisopropyl amide 作用下，以四氢呋喃为溶剂，反应 0.5h，以79%的产率得到(5E,7E,9E,13E)-1-[(4R,5R)-5-[(3aR,4R,6R,7aR)-6-[(1S,2R,6R)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylidene-1-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(benzenesulfonyl)hexadeca-5,7,9,13,15-pentaen-1-ol

参考文献：

名称：

两性酚3的C31-C67片段的合成

摘要：

DOI：

10.1002/anie.200602742
作为产物：

描述：

在吡啶、 2,6-二甲基吡啶、 sodium periodate 、四氧化锇、正丁基锂、 zinc(II) tetrahydroborate 、 LiDBB 、戴斯-马丁氧化剂、 N-甲基吗啉氧化物、 N,N-二异丙基乙胺作用下，以四氢呋喃、乙醚、正己烷、二氯甲烷、水、丙酮为溶剂，反应 131.97h，生成 (4S,5R)-5-[(3aR,4R,6R,7aR)-6-[(1S,2R,6R)-6-[(3aR,4R,6R,7aR)-4-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylidene-1-(2-trimethylsilylethoxymethoxy)hexyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

参考文献：

名称：

两性酚3的C31-C67片段的合成

摘要：

DOI：

10.1002/anie.200602742

点击查看最新优质反应信息

文献信息

Synthesis of the C31–C67 Fragment of Amphidinol 3

作者：Javier de Vicente、John R. Huckins、Scott D. Rychnovsky

DOI：10.1002/anie.200602742

日期：2006.11.6

同类化合物

苄基二亚苄基-α-D-甘露吡喃糖苷苄基2-C-甲基-3,4-O-(1-甲基亚乙基)-BETA-D-吡喃核糖苷艾日布林中间体,艾瑞布林中间体艾日布林中间体脱氧青蒿素甲基6-脱氧-3,4-O-异亚丙基-beta-L-甘油-吡喃己糖苷甲基3,4-异亚丙基-beta-L-阿拉伯糖吡喃糖苷甲基3,4-O-异亚丙基-beta-L-赤式-吡喃戊-2-酮糖甲基3,4-O-(氧代亚甲基)-beta-D-吡喃半乳糖苷甲基 3,4-O-异亚丙基吡喃戊糖苷甲基 2,3-O-羰基-4,6-O-异亚丙基-alpha-D-吡喃甘露糖苷果糖二丙酮氯磺酸酯果糖二丙酮托吡酯杂质7 托吡酯N-甲基杂质托吡酯-¹³C₆ 托吡酯史氏环氧化恶唑烷酮甲基催化剂双丙酮半乳糖双丙酮-L-阿拉伯糖六氢二螺[环己烷-1,2'-[1,3]二氧杂环戊并[4,5]吡喃并[3,2-d][1,3]二恶英-8',1''-环己烷]-4'-醇 [(3aS,5aR,7R,8aR,8bS)-7-(羟基甲基)-2,2,7-三甲基四氢-3aH-二[1,3]二氧杂环戊并[4,5-b:4',5'-d]吡喃-3a-基]甲基氨基磺酸 D-半乳醛环3,4-碳酸 6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷 6-叠氮基-6-脱氧-1,2:3,4-二-o-异亚丙基-d-半乳糖吡喃糖苷 6-O-乙酰基-1,2:3,4-二-O-异亚丙基-alpha-D-吡喃半乳糖 4,5-O-(1-甲基乙亚基)-beta-D-吡喃果糖 3alpha-羟基去氧基蒿甲醚 3-羟基去oxydihydroartemisinin 3,5,11-三氧杂-10-氮杂三环[6.2.1.02,6]十一碳-2(6),7,9-三烯 3,4-O-异亚丙基-L-阿拉伯糖 3,4-O-(苯基亚甲基)-D-核糖酸 D-内酯 3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 2,6-脱水-5-脱氧-3,4-O-(氧代亚甲基)-1-O-(三异丙基硅烷基)-D-阿拉伯糖-己-5-烯糖 2,3:4,6-二-o-异亚丙基-d-甘露糖苷甲酯 2,3:4,5-二-O-(1-甲基亚乙基)-beta-D-吡喃果糖甲基((((1-(甲硫基)亚乙基)氨基)氧基)羰基)酰胺基亚硫酸酯 2,3:4,5-二-O-(1-甲基亚乙基)-beta-D-吡喃果糖 1-叠氮基硫酸酯 2,3-脱异亚丙基托吡酯 2,3-O-羰基-alpha-d-吡喃甘露糖 2,3-O-(1-甲基亚乙基)-beta-D-吡喃果糖1-氨基磺酸酯 2,3-4,5-二-O-异亚丙基-1-O-甲基-beta-吡喃果糖 2,3,5-三邻苄基-1-o-(4-硝基苯甲酰基)-d-阿拉伯呋喃糖 2,2,2',2'-四甲基四氢螺[1,3-二氧戊环-4,6'-[1,3]二氧杂环戊并[4,5-c]吡喃]-7'-醇 10-乙氧基-1,5,9-三甲基-11,14,15-三氧杂四环[10.2.1.04,13.08,13]十五烷 1-{[(1R,2S,6R)-4,4-二甲基-3,5,10,11-四氧杂三环[6.2.1.02,6]十一烷-7-基]氧基}-3-{[(1S,2R,6S)-4,4-二甲基-3,5,10,11-四氧杂三环[6.2.1.02,6]十一烷-7-基]氧基}-2-丙胺 1-[(3aS,5aR,8aR,8bS)-2,2,7,7-四甲基四氢-3aH-二[1,3]二氧杂环戊并[4,5-b:4',5'-d]吡喃-3a-基]甲胺 1-O-ACETYL-2,3,4,6-DI-O-ISOPROPYLIDENE-Α-D-MANNOPYRANOSE1-O-乙酰基-2,3,4,6-二-O-异亚丙基-Α-D-吡喃甘露糖 1-O-ACETYL-2,3,4,6-DI-O-ISOPROPYLIDENE-Α-D-MANNOPYRANOSE1-O-乙酰基-2,3,4,6-二-O-异亚丙基-Α-D-吡喃甘露糖 1,6-脱水-2,3-O-异亚丙基-β-D-甘露吡喃糖 1,6-去氢-2,3-O-亚苄基-beta-D-吡喃甘露糖