5-O-(Trimethylsilyl)-6,7-O-isopropylidene-2,3-dideoxy-D-arabino-hept-2-enono-1,4-lactone | 132046-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(Trimethylsilyl)-6,7-O-isopropylidene-2,3-dideoxy-D-arabino-hept-2-enono-1,4-lactone
• 英文别名: (2R)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-2H-furan-5-one
• CAS: 132046-98-1
• 化学式: C₁₃H₂₂O₅Si
• 分子量: 286.4
• InChiKey: AKFLBKPTUDVPBX-FOGDFJRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-(Trimethylsilyl)-6,7-O-isopropylidene-2,3-dideoxy-D-arabino-hept-2-enono-1,4-lactone 在 二环己烷并-18-冠醚-6 、 potassium permanganate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2,3:6,7-Di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Ascent of the aldose series by four carbon atoms: total synthesis of D-glycero-D-talo-L-talo-undecose pentaacetonide

  摘要：

  Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1). The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving C(n+4) butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9. At the end of the eight-step sequence, undecose 9 was prepared in a 5.1% overall yield, which corresponded to a 69.5% average yield per step.

  DOI：

  10.1021/jo00006a032
• 作为产物：
  描述：

  三甲基氯硅烷 、 三甲硅氧基-2-呋喃 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 吡啶 、 三氟化硼乙醚 作用下， 生成 5-O-(Trimethylsilyl)-6,7-O-isopropylidene-2,3-dideoxy-D-ribo-hept-2-enono-1,4-lactone 、 5-O-(Trimethylsilyl)-6,7-O-isopropylidene-2,3-dideoxy-D-arabino-hept-2-enono-1,4-lactone
  参考文献：
  名称：

  Ascent of the aldose series by four carbon atoms: total synthesis of D-glycero-D-talo-L-talo-undecose pentaacetonide

  摘要：

  Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1). The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving C(n+4) butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9. At the end of the eight-step sequence, undecose 9 was prepared in a 5.1% overall yield, which corresponded to a 69.5% average yield per step.

  DOI：

  10.1021/jo00006a032

文献信息

• RASSU, GLORIA;CASIRAGHI, GIOVANNI;COLOMBO, LINO, 8TH INT. IUPAC CONF. ORG. SYNTH., HELSINKI, 23-27 JULY, 1990: ABSTR., HEL+
  作者：RASSU, GLORIA、CASIRAGHI, GIOVANNI、COLOMBO, LINO

  DOI：——

  日期：——
• CASIRAGHI, GIOVANNI;COLOMBO, LINO;RASSU, GLORIA;SPANU, PIETRO, J. ORG. CHEM., 56,(1991) N, C. 2135-2139
  作者：CASIRAGHI, GIOVANNI、COLOMBO, LINO、RASSU, GLORIA、SPANU, PIETRO

  DOI：——

  日期：——
• Ascent of the aldose series by four carbon atoms: total synthesis of D-glycero-D-talo-L-talo-undecose pentaacetonide
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu

  DOI：10.1021/jo00006a032

  日期：1991.3

  Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1). The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving C(n+4) butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9. At the end of the eight-step sequence, undecose 9 was prepared in a 5.1% overall yield, which corresponded to a 69.5% average yield per step.