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(2S,4S,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol | 82415-18-7

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

(2S,4S,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol

英文别名

(2R,3S,6S,8S,10S)-(+)-10-diphenyl-tbutylsiloxy-8-hydroxymethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane；(2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsiloxy-8-hydroxy-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane；(2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsiloxy-8-hydroxy-2,3-dimethyl-1,7-dioxaspiro[5.5]undecane；[(2S,4S,6S,8R,9S)-4-[tert-butyl(diphenyl)silyl]oxy-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]methanol

(2S,4S,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol化学式

CAS

82415-18-7

化学式

C₂₈H₄₀O₄Si

mdl

——

分子量

468.709

InChiKey

RFNBQDHRNWXPIN-DFGFYBKUSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

533.0±50.0 °C(Predicted)
密度：

1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.63
重原子数：

33.0
可旋转键数：

5.0
环数：

4.0
sp3杂化的碳原子比例：

0.57
拓扑面积：

47.92
氢给体数：

1.0
氢受体数：

4.0

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
——	(2S,4S,6S,8R,9S)-4-[tert-butyl(diphenyl)silyl]oxy-8,9-dimethyl-1,7-dioxaspiro[5.5]undecane-2-carbaldehyde	82415-05-2	C₂₈H₃₈O₄Si	466.693
——	(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester	105087-23-8	C₂₉H₄₀O₅Si	496.719
——	(2S,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate	102140-79-4	C₂₉H₄₀O₅Si	496.719
——	(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate	105087-22-7	C₂₉H₄₀O₅Si	496.719
——	methyl 2,4-dideoxy-3-O-diphenyl-t-butylsilyl-6-O-benzyl-α- and β-D-threo-hexopyranosides	94371-09-2	C₃₀H₃₈O₄Si	490.715
——	2,4-dideoxy-3-O-diphenyl-t-butylsilyl-6-O-benzyl-α- and β-D-threo-hexopyranoses	88096-38-2	C₂₉H₃₆O₄Si	476.688
——	(4S,6S)-3-diphenyl-t-butylsilyloxy-6-benzoyloxymethyltetrahydropyran-2-one	88096-40-6	C₂₉H₃₄O₄Si	474.672

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane	107692-12-6	C₂₉H₃₉NO₃Si	477.719
——	2-[(2S,4S,6R,8R,9S)-4-[tert-butyl(diphenyl)silyl]oxy-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]acetaldehyde	104705-91-1	C₂₉H₄₀O₄Si	480.72
——	(2S,4S,6S,8R,9S)-4-[tert-butyl(diphenyl)silyl]oxy-8,9-dimethyl-1,7-dioxaspiro[5.5]undecane-2-carbaldehyde	82415-05-2	C₂₈H₃₈O₄Si	466.693
——	(2'R,3'S,6'S,8'R,10'R)-(E)-(+)-4-(10'diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2-methylbut-2-enol	107692-08-0	C₃₂H₄₆O₄Si	522.8
——	(2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane	107692-09-1	C₃₂H₄₅IO₃Si	632.697
——	(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enol	112320-69-1	C₃₅H₅₂O₄Si	564.881
——	(2'R,3'S,6'S,8'S,10'R)-(E)-(+)-ethyl 4-(10'diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecane-8'-yl)-2-methylbut-2-enoate	107692-07-9	C₃₄H₄₈O₅Si	564.838
——	Methanesulfonic acid (E)-4-[(2R,4S,6R,8R,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-but-2-enyl ester	112995-99-0	C₃₃H₄₈O₆SSi	600.892
——	(1RS,5R,2'R,3'S,6'S,8'S,10'S)-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-3,5-dimethyl-6-thiophenylhex-2-enol	101212-42-4	C₄₁H₅₆O₄SSi	673.045
——	(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan	101212-44-6	C₄₁H₅₆O₃SSi	657.045
——	(2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane	107865-54-3	C₃₅H₄₆O₆SSi	622.898
——	(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'-phenylsulphonylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan	101212-45-7	C₄₁H₅₆O₅SSi	689.044
——	(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enyl toluene-p-sulphonate	113016-73-2	C₄₂H₅₈O₆SSi	719.07
——	(3RS,5R,2'R,3'S,6'S,8'S,10'R)-O-3-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1'7'-dioxaspiro<5.5>undecan-8'-yl)-3,5-dimethyl-6-thiophenylhex-1-enyl S-methyl thiocarbonate	112995-98-9	C₄₃H₅₈O₄S₃Si	763.215
——	(2R,2'R,3'S,6'S,8'R,10'R)-2,4-dimethyl-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8-yl)-hex-4-enoyl 4S-(propan-2-yl)oxazolidin-2-one	107692-10-4	C₄₁H₅₉NO₆Si	690.008
——	methyl 2-<(6'R)-(10-diphenyl-t-butylsiloxy-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan-8-yl)-6',8'-dimethyldecan-2',4',8'-trien-2'-yl>-4-methoxy-5-methylbenzoate	101212-47-9	C₄₉H₆₆O₆Si	779.145
——	2-{(1E,7E)-(R)-4-Benzenesulfonyl-3-benzoyloxy-9-[(2R,4S,6R,8R,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,5,7-trimethyl-nona-1,7-dienyl}-4-methoxy-5-methyl-benzoic acid methyl ester	101212-46-8	C₆₂H₇₆O₁₀SSi	1041.43

反应信息

作为反应物：

描述：

(2S,4S,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol 在咪唑、草酰氯、二甲基亚砜、三乙胺作用下，以四氢呋喃、吡啶、 N,N-二甲基甲酰胺为溶剂，反应 2.17h，生成 (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

参考文献：

名称：

Baker, Raymond; O'Mahony, Mary J.; Swain, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1623 - 1634

摘要：

DOI：
作为产物：

描述：

1,6-anhydro-2,4-dideoxy-3-O-allyl-β-D-threo-hexopyranose 在 10% palladium on active carbon 甲醇、 Wilkinson's catalyst 、甲酸、 Amberlite IR 118 、 Celite 、 camphor-10-sulfonic acid 、氢气、 potassium hydride 、 sodium hydride 、 silver carbonate 作用下，以乙醇、二氯甲烷为溶剂，反应 1.0h，生成 (2S,4S,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-methanol

参考文献：

名称：

螺缩醛的化学。手性二取代内酯衍生物的制备；合成阿维菌素和米尔倍霉素螺缩醛部分的关键中间体

摘要：

从葡糖葡聚糖已经开发了两个双保护的（4S，6S）-4-羟基-6-羟甲基四氢吡喃-2-酮的合成。与取代的乙炔锂衍生物随后氢化和酸催化的环化这些内酯的反应，导致形成的米尔倍霉素的螺缩醛部分的β 1和β 3。

DOI：

10.1039/c39830000829

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文献信息

The total synthesis of (+)-milbemycin β<sub>3</sub>

作者：Raymond Baker、Mary J. O'Mahony、Christopher J. Swain

DOI：10.1039/c39850001326

日期：——

We report the total synthesis of (+)-milbemycin β3 from the optically pure precursors spiroacetal (3) and vinyl iodide (2), and the aromatic aldehyde (4).

我们报告的全合成（+） -米尔倍霉素β 3从光学纯前体的螺缩醛（3）和碘乙烯（2），该芳香族醛（4）。
Total synthesis of (+)-milbemycin .beta.3

作者：Anthony G. M. Barrett、Robin A. E. Carr、Stephen V. Attwood、Geoffrey Richardson、Nigel D. A. Walshe

DOI：10.1021/jo00375a017

日期：1986.12
Baker, Raymond; Boyes, R. Hugh O.; Broom, D. Mark P., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1613 - 1622

作者：Baker, Raymond、Boyes, R. Hugh O.、Broom, D. Mark P.、O'Mahony, Mary J.、Swain, Christopher J.

DOI：——

日期：——
Total synthesis of milbemycin .beta.3

作者：D. R. Williams、B. A. Barner、K. Nishitani、J. G. Phillips

DOI：10.1021/ja00381a049

日期：1982.8
BAKER, RAYMOND;BOYES, R. HUGH O.;BROOM, D. MARK P.;OMAHONY, MARY J.;SWAIN+, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 7, 1613-1621

作者：BAKER, RAYMOND、BOYES, R. HUGH O.、BROOM, D. MARK P.、OMAHONY, MARY J.、SWAIN+

DOI：——

日期：——