2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
中文名称
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中文别名
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英文名称
2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
英文别名
Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trichloroethanimidate
CAS
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化学式
C36H36Cl3NO6
mdl
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分子量
685.044
InChiKey
LMICALCPRSCSMO-ZYSDIQSLSA-N
BEILSTEIN
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EINECS
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物化性质
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计算性质
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ADMET
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安全信息
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SDS
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制备方法与用途
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上下游信息
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文献信息
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表征谱图
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同类化合物
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相关功能分类
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相关结构分类
计算性质
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辛醇/水分配系数(LogP)：7.5
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重原子数：46
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可旋转键数：15
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环数：5.0
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sp3杂化的碳原子比例：0.31
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拓扑面积：79.2
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氢给体数：1
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氢受体数：7
上下游信息
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上游原料
中文名称 英文名称 CAS号 化学式 分子量 甲基2,3,4,6-四-O-苄基-D-吡喃甘露糖苷 methyl 2,3,4,6-tetra-O-benzyl-D-mannopyranoside 83462-67-3 C35H38O6 554.683 —— 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside —— C34H36O6 540.656 —— 2,3,4,6-tetra-O-benzyl-D-mannopyranose —— C34H36O6 540.656 —— 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 94943-10-9 C36H38O7 582.694 —— β-D-mannopyranose pentaacetate —— C16H22O11 390.344 Α-D-五乙酸甘露糖酯 D-Mannose pentaacetate 25941-03-1 C16H22O11 390.344 -
下游产品
中文名称 英文名称 CAS号 化学式 分子量 —— tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 128745-66-4 C38H44O6 596.764 —— methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside —— C62H66O11 987.199 —— methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside —— C62H66O11 987.199 —— methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl α-D-mannopyranosyl) α-D-glucopyranoside —— C62H66O11 987.199 —— cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 129894-49-1 C40H46O6 622.802 —— cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 129894-48-0 C40H46O6 622.802 —— (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran —— C35H38O6 554.683 —— cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 128820-59-7 C41H48O6 636.829 —— cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 128820-60-0 C41H48O6 636.829 —— methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-6-O-benzyl-4-O-(4-chlorobenzyl)-β-D-glucopyranoside 294637-41-5 C55H59ClO11 931.52 —— 2,3,4,6-tetra-O-benzyl-D-mannopyranose —— C34H36O6 540.656 —— benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 89615-39-4 C41H42O6 630.781 —— 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 117841-67-5 C46H54O11 782.928 —— methyl [2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside-(1->2)]-6-O-benzyl-3-O-(4-bromobenzyl)-4-O-(4-chlorobenzyl)-β-D-glucopyranoside 294637-40-4 C62H64BrClO11 1100.54 —— methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→2)-4,6-O-benzylidene-α-D-glucopyranoside —— C55H58O11 895.059 —— benzyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside 83866-15-3 C50H56O10 816.989 —— 1,6-anhydro-2,3,4-tri-O-benzoyl-β-D-glucopyranose 23567-05-7 C27H22O8 474.467 —— cholesterol 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 41736-89-4 C61H80O6 909.303 —— dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 90357-98-5 C48H49O9P 800.885 —— methyl (2R)-2-azido-3-[4-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyphenyl]propanoate 1428318-07-3 C44H45N3O8 743.857 - 1
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反应信息
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作为反应物：描述：2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 碘苯二乙酸 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以52%的产率得到(3aR,5R,6R,7S,7aS)-6,7,7a-tris(benzyloxy)-5-((benzyloxy)methyl)-2-(trichloromethyl)-3a,6,7,7a-tetrahydro-5H-pyrano[3,2-d]oxazole参考文献：名称：Visible-Light-Mediated β-C(sp3)–H Amination of Glycosylimidates: En Route to Oxazoline-Fused/Spiro Nonclassical Bicyclic Sugars摘要：A straightforward route has been developed for the diastereoselective synthesis of nonclassical conformationally constrained oxazoline-fused and Spiro bicyclic sugars bearing a quaternary center via selective beta-C-H amination of appropriately positioned glycosylimidates. The desired transformation proceeds via the generation of imidate N-radicals under visible-light conditions followed regioselective intramolecular N-C bond formation. The reactions tolerate broad functional groups under the optimized conditions. Furthermore, the synthetic utility of oxazoline-fused bicyclic sugar moiety is demonstrated through the glycosylation reactions.DOI：10.1021/acs.orglett.9b00763
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作为产物：