L-rhamnopyranose - CAS号 73-34-7

物化性质

物理描述：

Solid
熔点：

122°C
碰撞截面：

146.3 Å² [M+Na]+ [CCS Type: DT, Method: stepped-field]

计算性质

辛醇/水分配系数(LogP)：

-2.1
重原子数：

11
可旋转键数：

0
环数：

1.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

90.2
氢给体数：

4
氢受体数：

5

ADMET

代谢

L-鼠李糖是槲皮素的一个已知的人体代谢物。

L-Rhamnose is a known human metabolite of Quercitrin.

来源:NORMAN Suspect List Exchange

SDS

SDS：5c5af6d85e0cb63169a930132811e694

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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
——	rhamnopyranose	97466-79-0	C₆H₁₂O₅	164.158
——	rhamnose	——	C₆H₁₂O₅	164.158
——	3-O-methyl-L-rhamnopyranose	523-75-1	C₇H₁₄O₅	178.185
——	O²-methyl-L-6-deoxy-mannose	32077-86-4	C₇H₁₄O₅	178.185
——	Methyl O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside	71348-37-3	C₁₃H₂₄O₉	324.328
——	O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose	——	C₁₂H₂₂O₁₀	326.301
——	4,6-decadiyne-1-O-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside	1227937-36-1	C₂₂H₃₄O₁₀	458.506
——	α-L-rhamnopyranosyl-(1-3)-O-α-L-rhamnopyranosyl-(1-2)-D-glucopyranose	——	C₁₈H₃₂O₁₄	472.444
——	muricatic acid A	114892-47-6	C₄₀H₇₂O₁₉	857.0
——	operculinic acid C	126642-32-8	C₄₀H₇₂O₁₉	857.0
——	Operculinic acid E	126465-33-6	C₄₀H₇₂O₂₀	873.0
——	cuscutic acid B	——	C₃₇H₆₆O₂₀	830.919
——	cuscutic acid D	——	C₄₀H₇₂O₂₁	888.999
——	cuscutic acid A	——	C₃₈H₆₈O₂₁	860.945
——	cuscutic acid C	——	C₃₈H₆₈O₂₀	844.946
——	simonic acid B	——	C₄₆H₈₂O₂₃	1003.14
——	simonic acid A	1137099-42-3	C₄₆H₈₂O₂₄	1019.14
——	(11S)-jalapinolic acid 11-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-[α-L-rhamnopyranosyl-(1->4)]-O-[α-L-rhamnopyranosyl-(1->2)]-β-D-fucopyranoside	120583-62-2	C₄₆H₈₂O₂₄	1019.14
——	(S)-12-hydroxypentadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside	1400908-78-2	C₄₅H₈₀O₂₅	1021.12
——	(S)-12-hydroxyheptadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside	1400908-80-6	C₄₇H₈₄O₂₅	1049.17
——	(S)-12-hydroxyhexadecanoic acid 12-O-β-D-glucopyranosyl-(1->3)-O-[α-L-rhamnopyranosyl-(1->4)]-O-α-L-rhamnopyranosyl-(1->4)-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside	1400908-79-3	C₄₆H₈₂O₂₅	1035.14
——	methyl ester of simonic acid B	——	C₄₇H₈₄O₂₃	1017.17
——	quamoclinic acid H	1287249-85-7	C₆₂H₁₀₈O₃₉	1477.52
——	quamoclinic acid G	1287249-64-2	C₅₆H₉₈O₃₅	1331.37
——	6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glucofuranoside	32785-99-2	C₁₂H₂₀O₅	244.288
——	descinnamoyl mussatioside I	110241-08-2	C₂₅H₃₈O₁₅	578.568
——	α-L-rhamnopyranosido-(1<*>5)-D-3-deoxy-D-manno-2-octulosonic acid	——	C₁₄H₂₄O₁₂	384.337
——	albinoside I	1400878-57-0	C₅₁H₈₆O₂₆	1115.23

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下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	rhamnose	——	C₆H₁₂O₅	164.158
——	6-deoxy-L-talose	——	C₆H₁₂O₅	164.158
甲基-Alpha-D-吡喃鼠李糖苷	methyl 6-deoxy-α-L-mannopyranoside	14917-55-6	C₇H₁₄O₅	178.185
——	(2S,3R,4R,5R,6S)-2-Methoxy-6-methyl-tetrahydro-pyran-3,4,5-triol	42214-00-6	C₇H₁₄O₅	178.185
甲基6-脱氧吡喃己糖苷	methyl L-rhamnopyranoside	63864-94-8	C₇H₁₄O₅	178.185
——	methyl 6-deoxy-α-L-glucoside	——	C₇H₁₄O₅	178.185
——	methyl 6-deoxy-α-L-talopyranoside	2592-55-4	C₇H₁₄O₅	178.185
——	methyl 6-deoxy-β-L-glucopyranoside	——	C₇H₁₄O₅	178.185
——	n-butyl-1-O-α-L-rhamnopyranoside	83161-20-0	C₁₀H₂₀O₅	220.266
——	butyl L-rhamnopyranoside	1198580-43-6	C₁₀H₂₀O₅	220.266
——	pentyl-rhamnoside	83161-22-2	C₁₁H₂₂O₅	234.293
——	2-pentyl α-L-rhamnopyranoside	1621700-70-6	C₁₁H₂₂O₅	234.293
——	1-dodecyl L-rhamnopyranoside	494844-54-1	C₁₈H₃₆O₅	332.481
——	1-hexadecyl α-L-rhamnopyranoside	446302-45-0	C₂₂H₄₄O₅	388.588
——	hexadecyl L-rhamnopyranoside	——	C₂₂H₄₄O₅	388.588
——	octyl α-L-rhamnopyranoside	258353-77-4	C₁₄H₂₈O₅	276.373
——	1-octyl L-rhamnopyranoside	——	C₁₄H₂₈O₅	276.373
——	decyl L-rhamnopyranoside	——	C₁₆H₃₂O₅	304.427
——	1-decyl L-rhamnopyranoside	1584693-56-0	C₁₆H₃₂O₅	304.427
——	1-tetradecyl L-rhamnopyranoside	1584693-64-0	C₂₀H₄₀O₅	360.535
——	eicosyl α-L-rhamnoside	1621700-86-4	C₂₆H₅₂O₅	444.696
——	2-hexyl α-L-rhamnopyranoside	1621700-73-9	C₁₂H₂₄O₅	248.32
——	2-octyl α-L-rhamnopyranoside	1621700-80-8	C₁₄H₂₈O₅	276.373
——	tert-butyl α-L-rhamnopyranoside	——	C₁₀H₂₀O₅	220.266
——	4-methyl-2-pentyl α-L-rhamnopyranoside	1621700-75-1	C₁₂H₂₄O₅	248.32
——	allyl α-L-rhamnopyranoside	64650-81-3	C₉H₁₆O₅	204.223
——	allyl β-L-rhamnopyranoside	——	C₉H₁₆O₅	204.223
——	allyl rhamnoside	——	C₉H₁₆O₅	204.223
——	O-(2-aminoethyl)-α-L-rhamnopyranose	1206451-84-4	C₈H₁₇NO₅	207.227
——	O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose	——	C₁₂H₂₂O₁₀	326.301
——	methyl 2,3,4-tri-O-methyl-L-rhamnopyranoside	14200-00-1	C₁₀H₂₀O₅	220.266
——	methyl 2,6-dideoxy-α-L-ribo-hexopyranoside	78853-88-0	C₇H₁₄O₄	162.186
——	methyl-2,6-didesoxy-α-L-arabino-hexopyranoside	19131-10-3	C₇H₁₄O₄	162.186
——	methyl 3-O-allyl-α-L-rhamnopyranoside	——	C₁₀H₁₈O₅	218.25
——	methyl O-β-D-ribofuranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside	——	C₁₈H₃₂O₁₃	456.444
——	O-β-D-ribofuranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->3)-L-rhamnopyranose	——	C₁₇H₃₀O₁₃	442.417
——	methyl O-β-D-ribofuranosyl-(1->3)-α-L-rhamnopyranoside	——	C₁₂H₂₂O₉	310.301
——	(2R,3R,4R,5R,6S)-2-(2-azidoethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol	1381853-30-0	C₈H₁₅N₃O₅	233.224
——	2,3-O-isopropylidene-L-rhamnnopyranose	——	C₉H₁₆O₅	204.223
——	allyl 4-O-β-D-galactopyranosyl-3-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside	——	C₂₁H₃₆O₁₅	528.508
甲基 2,3-O-异亚丙基-alpha-L-吡喃鼠李糖苷	methyl 2,3-O-isopropylidene-α-L-rhamnoside	14133-63-2	C₁₀H₁₈O₅	218.25
——	methyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside	24562-43-4	C₁₀H₁₈O₅	218.25
——	daumone	690991-47-0	C₁₃H₂₄O₆	276.33
——	2,3,4-tri-O-acetyl-α-L-rhamnopyranose	28915-80-2	C₁₂H₁₈O₈	290.27
——	methyl α-L-mycaroside	18424-67-4	C₈H₁₆O₄	176.213
——	allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside	——	C₁₂H₂₀O₅	244.288
——	methyl 2,3-O-methylorthoacetyl α-L-rhamnopyranoside	406460-49-9	C₁₁H₂₀O₆	248.276
——	(2S,3R,4S,5S)-2,3-(propane-2,2-dioxy)hexane-1,4,5-triol	162932-15-2	C₉H₁₈O₅	206.239
——	α-L-talopyranoside, methyl 6-deoxy-,2,3,4-triacetate	2592-54-3	C₁₃H₂₀O₈	304.297
——	2,3-O-isopropylidene-L-rhamnofuranose	112245-58-6	C₉H₁₆O₅	204.223
——	2,3-O-isopropylidene-α-L-rhamnofuranose	52572-04-0	C₉H₁₆O₅	204.223
——	2,3-O-isopropylidene-β-L-rhamnofuranose	14133-65-4	C₉H₁₆O₅	204.223
——	6-(benzyloxy)-6-oxohexyl 6-deoxy-β-L-mannopyranoside	908860-78-6	C₁₉H₂₈O₇	368.427
——	benzyl α-L-rhamnopyranoside	——	C₁₃H₁₈O₅	254.283
——	benzyl β-L-rhamnopyranoside	292619-83-1	C₁₃H₁₈O₅	254.283
——	allyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside	——	C₁₃H₂₂O₆	274.314
——	methyl 4-O-benzyl-α-L-rhamnopyranoside	25019-69-6	C₁₄H₂₀O₅	268.31
——	methyl 2-O-benzyl-α-L-rhamnopyranoside	75336-81-1	C₁₄H₂₀O₅	268.31
DHR催化剂	(+)-(2S,3S,4S)-t-2-methyltetrahydropyran-r-3,t-4-diol	89614-50-6	C₆H₁₂O₃	132.159
2,3,4-三-O-苄基-L-吡喃鼠李糖	2,3,4-tri-O-benzyl-L-rhamnopyranose	210426-02-1	C₂₇H₃₀O₅	434.532
——	2,3,4-tri-O-benzyl-α-L-rhamnopyranose	86795-38-2	C₂₇H₃₀O₅	434.532
——	1,2,3,4-tetra-O-acetyl-L-rhamnopyranose	30021-94-4	C₁₄H₂₀O₉	332.307
——	1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose	30021-94-4	C₁₄H₂₀O₉	332.307
——	1,2,3,4-tetra-O-acetyl-6-deoxy-β-L-glucopyranose	36807-81-5	C₁₄H₂₀O₉	332.307
——	methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside	69558-07-2	C₂₁H₂₆O₅	358.434
——	(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol	69850-47-1	C₂₁H₂₆O₅	358.434
——	allyl 4-O-benzyl-α-L-rhamnopyranoside	89821-78-3	C₁₆H₂₂O₅	294.348
——	methyl O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside	144174-61-8	C₄₁H₄₈O₉	684.827
——	allyl 3,4-di-O-benzyl-α-L-rhamnopyranoside	119471-45-3	C₂₃H₂₈O₅	384.472
——	methyl 3-O-allyl-2,4-di-O-benzyl-α-L-rhamnopyranoside	135041-31-5	C₂₄H₃₀O₅	398.499
——	allyl 2,4-di-O-benzyl-α-L-rhamnopyranoside	124943-18-6	C₂₃H₂₈O₅	384.472

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反应信息

作为反应物：

描述：

L-rhamnopyranose 在 sodium tetrahydroborate 作用下，生成 rhamnitol

参考文献：

名称：

Characterization of 6-deoxy-d-altritol in the cell-wall polysaccharide of Nocardia asteroides R 399

摘要：

A polyol, found in the cell-wall of Nocardia asteroides R 399 as a component of a neutral polysaccharide mainly composed of D-arabinose and D-galactose, was identified by mass spectrometry, paper chromatography, thin-layer chromatography, and gas chromatography as 6-deoxy-D-altritol.

DOI：

10.1016/s0008-6215(00)90459-2
作为产物：

描述：

柚皮苷在 α-L-rhamnosidase from Pichia angusta X349 作用下，以 acetate buffer 为溶剂，反应 18.0h，生成 L-rhamnopyranose

参考文献：

名称：

Purification and Characterization of an α-L-Rhamnosidase fromPichia angustaX349

摘要：

通过四个层析步骤，从 Pichia angusta X349 中纯化出了一种细胞内 α-L 鼠李糖苷酶。α-L-鼠李糖酶似乎是一种单体蛋白，分子量为 90 kDa。该酶的等电点为 4.9，在 pH 值为 6.0 和约 40°C 时具有最佳活性。L- 鼠李糖抑制 Ki 为 25 mM。该酶受 Cu2+、Hg2+ 和对氯脲苯甲酸盐的抑制。α-L-鼠李糖酶对α-L-吡喃鼠李糖苷具有高度特异性，能从柚皮苷、芦丁、橙皮苷和 3-槲皮苷中释放鼠李糖。α-L-鼠李糖苷酶在葡萄酒乙醇浓度下具有活性。它能从从麝香葡萄汁中提取的香味前体中有效释放单萜醇，如芳樟醇和香叶醇。

DOI：

10.1271/bbb.64.2179
作为试剂：

描述：

[(2R,3R,4S,5R)-3,4,5,6-tetrakis(butanoyloxy)oxan-2-yl]methyl butanoate 在 L-rhamnopyranose 作用下，以四氢呋喃、水为溶剂，反应 16.0h，以57%的产率得到[(2R,3R,4S,5R)-3,4,5-tris(butanoyloxy)-6-hydroxyoxan-2-yl]methyl butanoate

参考文献：

名称：

[EN] MULTIBIOTIC AGENTS AND METHODS OF USING THE SAME
[FR] AGENTS MULTIBIOTIQUES ET PROCÉDÉS D'UTILISATION DE CEUX-CI

摘要：

公开号：

WO2018226732A8

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文献信息

Synthesis and n.m.r.-spectral analysis of unenriched and [1-13C]-enriched 5-deoxypentoses and 5-O-methylpentoses

作者：Joseph R. Snyder、Anthony S. Serianni

DOI：10.1016/0008-6215(87)80180-5

日期：1987.6

preparing unenriched and [1-13C]-enriched 5-deoxy- and 5-O-methyl-pentoses in the D or L configuration. The 1H-n.m.r. spectra of these compounds have been interpreted, and the 13C-n.m.r. spectra assigned with the aid of 2-D 13C-1H chemical-shift correlation spectroscopy. Tautomeric forms (furanoses, hydrate, and aldehyde) in solution in 2H2O have been quantified with the aid of [1-13C]-enriched derivatives

描述了用于制备D或L构型的未富集和[1-13C]富集的5-脱氧和5-O-甲基戊糖的化学方法。解释了这些化合物的1H-nmr光谱，并借助2-D 13C-1H化学位移相关光谱法指定了13C-nmr光谱。在2H2O溶液中的互变异构形式（呋喃糖，水合物和醛）已通过富含[1-13C]的衍生物进行了定量。为了评估5-C-脱氧和5-O-甲基化对化学位移和偶联常数（1H-1H，13C- 1H和13C-13C）和戊呋喃糖构象。
一种药物缀合物和提高药物分子半衰期的方法

申请人：江南大学

公开号：CN110420334A

公开（公告）日：2019-11-08

本发明公开了一种药物缀合物和提高药物分子半衰期的方法，所述药物缀合物为药物分子被结合有半抗原的小分子修饰，所述半抗原是指存在内源性抗体的半抗原。本发明将半抗原分子修饰在药物分子上，被修饰后的药物分子可以和针对此类半抗原内源性抗体特异性结合，从而显著提升药物分子在体内的半衰期。
[EN] CARBOHYDRATE-MODIFIED GLYCOPROTEINS AND USES THEREOF<br/>[FR] GLYCOPROTÉINES MODIFIÉES PAR GLUCIDE ET LEURS UTILISATIONS

申请人：NEWLINK GENETICS CORP

公开号：WO2014151423A1

公开（公告）日：2014-09-25

The present invention provides immunogenic compounds which stimulate immune responses in a subject. The present invention provides compositions comprising an isolated glycoprotein antigen covalently bound at pre-existing carbohydrate residues present on the glycoprotein to a carbohydrate epitope. The present invention also provides a method to induce an immune response in a subject comprising administering the compounds of the invention. The present invention further provides methods of making the compounds of the invention and methods of using the compounds of the invention to stimulate immune responses to infectious disease agents and tumors.

本发明提供了刺激受试者免疫反应的免疫原化合物。本发明提供了包含一个孤立的糖蛋白抗原的组合物，该糖蛋白抗原以共价结合的方式结合在糖蛋白上已有的糖残基上，形成一个糖基表位。本发明还提供了一种诱导受试者免疫反应的方法，包括给予本发明的化合物。本发明还提供了制备本发明化合物的方法，以及利用本发明化合物刺激免疫反应以应对传染病和肿瘤的方法。
Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy

作者：Ying-Hsin Wang、Hsien-Wei Yeh、Hsiao-Wen Wang、Chia-Chun Yu、Jih-Hwa Guh、Der-Zen Liu、Pi-Hui Liang

DOI：10.1016/j.carres.2013.04.022

日期：2013.6

Naturally occurring spirostanol saponins bear a chacotriose, alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyr anose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2' and/or 4' positions of chacotriose is

天然存在的螺固醇皂苷带有低聚部分的三甘醇，α-L-鼠李糖基-（1-> 2）-[α-L-鼠李糖基-（1-> 4）]-β-D-葡萄糖吡喃糖残基。据信对于生物学活性是重要的。在本文中，描述了一种简明的组合方法的开发，该方法用于合成在chacotriose的2'和/或4'位置上的两个系列的聚糖变体，并研究了叶绿素在3-OH处的糖苷部分的结构-活性关系。发现这些化合物对白血病细胞系CCRF和HL-20的细胞毒性较弱，表明茶三糖部分对于抗癌活性很重要。
A Generalized Procedure for the One-Pot Preparation of Glycosyl Azides and Thioglycosides Directly from Unprotected Reducing Sugars under Phase-Transfer Reaction Conditions

作者：Rishi Kumar、Pallavi Tiwari、Prakas R. Maulik、Anup K. Misra

DOI：10.1002/ejoc.200500646

日期：2006.1

Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding

过氧乙酰化糖基叠氮化物和硫代糖苷直接从未保护的还原糖通过通用的一锅法在相转移条件下原位生成过氧乙酰化糖基溴化物，以优异的收率制备。在糖基溴化物的异头中心完全反转形成立体选择性产物，为制备 1,2-反式糖基叠氮化物和硫代糖苷提供了一种通用的高产率方法。（© Wiley-VCH Verlag GmbH & Co. KGaA， 69451 德国魏因海姆，2006）

L-rhamnopyranose | 73-34-7

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