[ CAS No. 2438-80-4 ] {[proInfo.proName]}

Name: 2438-80-4|(2S,3R,4R,5S)-2,3,4,5-Tetrahydroxyhexanal|98%
Brand: Ambeed
SKU: A101796
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2D 3D

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Quality Control of [ 2438-80-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2438-80-4 ]

SDS Specification

Alternatived Products of [ 2438-80-4 ]

Product Details of [ 2438-80-4 ]

CAS No. :	2438-80-4	MDL No. :	MFCD00135607
Formula :	C₆H₁₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PNNNRSAQSRJVSB-KCDKBNATSA-N
M.W :	164.16	Pubchem ID :	3034656
Synonyms :	6-Desoxygalactose;L-(-)-Fucose;Fucosse;(-)-L-Fucose;L-(−)-Fucose;L-fucopyranose;6-Deoxy-L-Galactose;L-Fucose;L-Galactomethylose

Calculated chemistry of [ 2438-80-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	35.8
TPSA :	97.99 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.03
Log Po/w (XLOGP3) :	-2.38
Log Po/w (WLOGP) :	-2.35
Log Po/w (MLOGP) :	-2.1
Log Po/w (SILICOS-IT) :	-1.1
Consensus Log Po/w :	-1.59

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.91
Solubility :	1320.0 mg/ml ; 8.05 mol/l
Class :	Highly soluble
Log S (Ali) :	0.86
Solubility :	1190.0 mg/ml ; 7.26 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	1.9
Solubility :	13000.0 mg/ml ; 79.3 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.11

Safety of [ 2438-80-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2438-80-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2438-80-4 ]
Downstream synthetic route of [ 2438-80-4 ]

[ 2438-80-4 ] Synthesis Path-Upstream 1~4

1
[ 64-19-7 ]
[ 41263-94-9 ]
[ 2438-80-4 ]
[ 63-42-3 ]

Reference： [1] Biochemical Journal, 1958, vol. 68, p. 708,710, 713
[2] Chemische Berichte, 1955, vol. 88, p. 1145

2
[ 7647-01-0 ]
[ 41263-94-9 ]
[ 2438-80-4 ]
[ 63-42-3 ]

Reference： [1] Biochemical Journal, 1958, vol. 68, p. 708,710, 713
[2] Chemische Berichte, 1955, vol. 88, p. 1145

3
[ 2438-80-4 ]
[ 13074-06-1 ]

Reference： [1] Tetrahedron Asymmetry, 2008, vol. 19, # 6, p. 739 - 745
[2] Chemische Berichte, 1913, vol. 46, p. 3655[3] Chem. Zentralbl., 1915, vol. 86, # I, p. 605
[4] Phytochemistry, 2002, vol. 61, # 4, p. 455 - 459
[5] Patent: US2010/105885, 2010, A1, . Location in patent: Page/Page column 15

4
[ 2438-80-4 ]
[ 13074-06-1 ]
[ 93697-45-1 ]
[ 3736-74-1 ]

Reference： [1] Carbohydrate Research, 1988, vol. 176, p. 145 - 148

[ 2438-80-4 ] Synthesis Path-Downstream 1~88

1
[ 110-86-1 ]
[ 2438-80-4 ]
[ 3616-21-5 ]

Reference： [1]Helvetica Chimica Acta,1937,vol. 20,p. 1529,1531

2
[ 64-17-5 ]
[ 2438-80-4 ]
[ 29964-95-2 ]
[ 93780-11-1 ]

Reference： [1]Chemische Berichte,1955,vol. 88,p. 1145

3
[ 74-90-8 ]
[ 2438-80-4 ]
L-glycero-D-manno-7-deoxy-heptonic acid [ No CAS ]
[ 776993-58-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 542

4
[ 2438-80-4 ]
[ 111-26-2 ]
L-fucose-hexylimine [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 77,86

5
[ 2438-80-4 ]
[ 111-68-2 ]
L-fucose-heptylimine [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 77,86

6
[ 2438-80-4 ]
[ 10151-46-9 ]
naphthalene-2-sulfonic acid-(6-deoxy-L-galactitol-1-ylidenehydrazide) [ No CAS ]

Reference： [1]Biochemische Zeitschrift,1954,vol. 326,p. 139,145

7
[ 2438-80-4 ]
[ 861569-09-7 ]
bis-{4-[(6-deoxy-L-galactitol-1-ylidene)-methyl-hydrazino]-phenyl}-methane [ No CAS ]

Reference： [1]Chemische Berichte,1917,vol. 50,p. 42
Chemisches Zentralblatt,1919,vol. 90,p. 1047

8
[ 2438-80-4 ]
[ 143-33-9 ]
L-glycero-D-manno-7-deoxy-heptonic acid [ No CAS ]
[ 776993-58-9 ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 3882
[2]Journal of the American Chemical Society,1950,vol. 72,p. 3882

9
[ 2438-80-4 ]
[ 59-88-1 ]
[ 2079-46-1 ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 3021

10
[ 2438-80-4 ]
[ 72358-76-0 ]
[ 2079-46-1 ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 3860
Chemisches Zentralblatt,1905,vol. 76,p. 1527

11
[ 2438-80-4 ]
[ 620-02-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1892,vol. 271,p. 91

12
[ 2438-80-4 ]
[ 13074-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Raney-nickel; at 50℃; under 9000.9 Torr;Product distribution / selectivity;	Example 10Production of 1-deoxy- and 6-deoxy D-tagatose from L-fucose (6-deoxy L-galactose) and the enantiomer D-fucose (6-deoxy D-galactose)Via a chemical reduction method with Raney-nickel (pressure at 1.2 MPa, agitation at 700 rpm, and a temperature of 50 C.), first, 6-deoxy L-galactitol and 6-deoxy D-galactitol were prepared from starting materials L-fucose and D-fucose, respectively. Subsequently, the galactitol was oxidized, and the resulting individual deoxy sugar alcohols as substrates were subjected to a reaction with washed bacterial cells [the composition for the bacterial cell reaction: bacterial cell at OD600=40; 50 mM Tris-HCl buffer (pH 8.0); substrate at 1%], using Enterobacter agglomerans strain 221e (FERM BP-4700) [cultured in a culture broth (erythritol at 1.0 w/v %, yeast extract at 0.5 w/v %, polypeptone at 0.5 w/v %, common salt at 0.5 w/v %, and glycerol at 1.0 w/v %) at 30 C. and collected and washed] (see JP-A-08-056659).The HPLC analysis results show that the bacterium oxidized and converted 6-deoxy L-galactitol to 1-deoxy D-tagatose or oxidized and converted 6-deoxy D-galactitol to 6-deoxy D-tagatose.The results of the oxidation of 6-deoxy L-galactitol and 6-deoxy D-galactitol using the bacterial strain indicate that the bacterial cell could recognize and convert the sugar structures despite the presence of methyl group at positions 1 and 6, preferentially to D-tagatose.

Reference： [1]Tetrahedron Asymmetry,2008,vol. 19,p. 739 - 745
[2]Chemische Berichte,1913,vol. 46,p. 3655
Chemisches Zentralblatt,1915,vol. 86,p. 605
[3]Phytochemistry,2002,vol. 61,p. 455 - 459
[4]Patent: US2010/105885,2010,A1 .Location in patent: Page/Page column 15

13
[ 2438-80-4 ]
[ 3616-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(ll) chloride;immobilized D-arabinose isomerase; at 40℃;pH 9;Enzymatic reaction; glycine-NaOH buffer;Product distribution / selectivity;	Example 24Production of 6-deoxy L-tagatoseThe reaction is for producing 6-deoxy L-tagatose by isomerizing 6-deoxy L-galactose, which corresponds to the reaction C numbered with 63-27 in FIG. 3.Under the following reaction conditions, L-fucose (6-deoxy L-galactose) was isomerized with D-arabinose isomerase, to produce 6-deoxy L-tagatose.<Reaction Conditions>Substrate: 10% L-fucose (6-deoxy L-galactose)Enzyme: immobilized D-arabinose isomeraseBuffer: 50 mM glycine-NaOH buffer (pH 9.0)Ion: 1 mM MnCl2 Temperature: 40 C.Separation was done by the following method.<Separation Method>Dowex 50W X2One-pass separation systemFIG. 52(a) shows HPLC after reaction, while FIG. 52(b) shows HPLC of the separated and purified product (6-deoxy L-tagatose). The optical rotation was +0.9. The 13C NMR spectrum is shown in FIG. 53.The reaction for the production of 6-deoxy L-tagatose from 6-deoxy L-galactose in this Example is shown in Chemical scheme 8.

Reference： [1]Helvetica Chimica Acta,1937,vol. 20,p. 1529,1531
[2]Journal of Biological Chemistry,1956,vol. 219,p. 557,562,565
[3]Patent: US2010/105885,2010,A1 .Location in patent: Page/Page column 22
[4]Biochimie,2012,vol. 94,p. 1926 - 1934
[5]Enzyme and Microbial Technology,2019,vol. 131

14
[ 2438-80-4 ]
[ 26372-13-4 ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 307

15
[ 2438-80-4 ]
[ 6035-60-5 ]

Reference： [1]Chemische Berichte,1917,vol. 50,p. 42
Chemisches Zentralblatt,1919,vol. 90,p. 1047

16
[ 2438-80-4 ]
[ 488-31-3 ]

Reference： [1]Chemische Berichte,1909,vol. 42,p. 2009
Chemisches Zentralblatt,1909,vol. 80,p. 591

17
[ 2438-80-4 ]
O¹,O²;O³,O⁴-dimethanediyl-α-L-fucopyranose [ No CAS ]

Reference： [1]Journal of the Chemical Society,1957,p. 2191

18
[ 2438-80-4 ]
[ 248256-29-3 ]

Reference： [1]Journal of Biological Chemistry,1922,vol. 54,p. 65,69

19
[ 2438-80-4 ]
[ 136572-16-2 ]

Reference： [1]Journal of the Chemical Society,1947,p. 1461,1463

20
[ 2438-80-4 ]
[ 52-89-1 ]
[ 152983-87-4 ]

Reference： [1]Carbohydrate Research,1989,vol. 187,p. 223 - 238

21
[ 2438-80-4 ]
[ 13074-06-1 ]
[ 93697-45-1 ]
[ 3736-74-1 ]

Reference： [1]Carbohydrate Research,1988,vol. 176,p. 145 - 148

22
[ 2438-80-4 ]
[ 103419-79-0 ]

Reference： [1]Carbohydrate Research,1986,vol. 155,p. 73 - 88

23
[ 2438-80-4 ]
[ 2627-86-3 ]
[ 108-24-7 ]
[ 79526-49-1 ]

Reference： [1]Carbohydrate Research,1982,vol. 107,p. 169 - 176

24
[ 2438-80-4 ]
[ 2627-86-3 ]
[ 108-24-7 ]
[ 79526-49-1 ]

Reference： [1]Chemistry Letters,1981,p. 943 - 946

25
[ 2438-80-4 ]
[ 108-24-7 ]
[ 7404-35-5 ]

Yield	Reaction Conditions	Operation in experiment
99.6%	With sodium acetate;Reflux;	EXAMPLE 2A To a boiling solution of acetic anhydride (35 mL) and NaOAc (2.5 g, 30.5 mmol) was added L-fucose (5 g, 30.5 mmol) in small portions. Once the solution became translucent, it was removed from the heat and partially solidified upon cooling. The residues were poured over crushed ice (50 g) and solid sodium bicarbonate was added until the evolution of gas ceased. The organic material was extracted into EtOAc (3×100 mL), washed with sodium bicarbonate (100 mL) and brine (100 mL) and dried over MgSO4. Removing the solvents under vacuum, resulted in a yellow syrup (10.1 g, 99.6%).
	With pyridine; at 0 - 20℃; for 22.17h;	1,2,3,4-Tetra-O-acetyl-L-fucopyranose Acetic anhydride (57 mL) was added over 10 minutes to a stirred solution of L-(-)-fucose (8.2 g) in pyridine (80 mL) at 0 C. After 2 hours the mixture was warmed to room temperature. After 20 hours the mixture was evaporated under reduced pressure and water (200 mL) added. The mixture was extracted with dichloromethane (4) and the combined extracts were washed with 1M hydrochloric acid (2), saturated sodium hydrogen carbonate (*2) and water, dried (MgSO4) and evaporated under reduced pressure to give compound 24 (15.6 g).

Reference： [1]Canadian Journal of Chemistry,1981,vol. 59,p. 2086 - 2095
[2]Patent: US9829481,2017,B2 .Location in patent: Page/Page column 11
[3]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2421 - 2439
[4]Tetrahedron Asymmetry,2005,vol. 16,p. 83 - 95
[5]Patent: US2009/176970,2009,A1 .Location in patent: Page/Page column 6
[6]Journal of the American Chemical Society,2016,vol. 138,p. 4938 - 4947

26
[ 84012-04-4 ]
[ 10257-28-0 ]
[ 2438-80-4 ]
[ 10486-91-6 ]
[ 134-61-2 ]

Reference： [1]Carbohydrate Research,1984,vol. 135,p. 342 - 348

27
[ 2438-80-4 ]
[ 108-24-7 ]
[ 6298-84-6 ]

Reference： [1]Analytical Chemistry,2004,vol. 76,p. 6566 - 6574

28
[ 2438-80-4 ]
[ 108-24-7 ]
[ 75-08-1 ]
[ 24807-88-3 ]

Reference： [1]Analytical Chemistry,2004,vol. 76,p. 6566 - 6574

29
[ 108-22-5 ]
[ 2438-80-4 ]
[ 136572-16-2 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 8965 - 8968

30
[ 108-22-5 ]
[ 2438-80-4 ]
[ 64913-16-2 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 8965 - 8968

31
[ 108-05-4 ]
[ 2438-80-4 ]
1,2:3,4-di-O-ethylidene-α-L-fucose [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 8965 - 8968

32
[ 2438-80-4 ]
tri-O-acetyl-β-L-fucopyranosylformaldoxime [ No CAS ]

Reference： [1]Synthetic Communications,2003,vol. 33,p. 1707 - 1715

33
[ 2438-80-4 ]
tri-O-acetyl-β-L-fucopyranosylformaldoxime [ No CAS ]

Reference： [1]Synthetic Communications,2003,vol. 33,p. 1707 - 1715

34
[ 2438-80-4 ]
tri-O-acetyl-β-L-fucopyranosylnitromethane [ No CAS ]

Reference： [1]Synthetic Communications,2003,vol. 33,p. 1707 - 1715

35
[ 2438-80-4 ]
(Z)-2,3,4-tri-O-acetyl-β-L-fucopyranosylformaldoxime [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8505 - 8513

36
[ 2438-80-4 ]
(E)-2,3,4-tri-O-acetyl-β-L-fucopyranosylformaldoxime [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8505 - 8513

37
[ 2438-80-4 ]
2,3,4-tri-O-acetyl-β-L-fucopyranosyl(nitro)methane [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8505 - 8513

38
[ 2438-80-4 ]
3,4-di(2,3,4,6-tetra-O-acetyl-β-L-fucopyranosyl)-1,2,5-oxadiazole 2-oxide [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8505 - 8513

39
[ 2438-80-4 ]
Acetic acid (1S,2R,3R,4S)-2,3,4-triacetoxy-1-((S)-3,5-diphenyl-2,3-dihydro-[1,3,4]thiadiazol-2-yl)-pentyl ester [ No CAS ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 12911 - 12922

40
[ 2438-80-4 ]
[ 117757-04-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1959,vol. 628,p. 186,189

41
[ 2438-80-4 ]
[ 5456-69-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1959,vol. 628,p. 186,189

42
[ 2438-80-4 ]
[ 54253-49-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1959,vol. 628,p. 186,189

43
[ 2438-80-4 ]
[ 488-28-8 ]

Reference： [1]Chemische Berichte,1913,vol. 46,p. 3655
Chemisches Zentralblatt,1915,vol. 86,p. 605

44
[ 2438-80-4 ]
L-glycero-D-manno-7-deoxy-heptonic acid-4-lactone [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 542

45
[ 2438-80-4 ]
L-glycero-D-gluco-7-deoxy-heptonic acid-4-lactone [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 542

46
[ 2438-80-4 ]
[ 17169-76-5 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4373,4376

47
[ 2438-80-4 ]
[ 17073-59-5 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4373,4376

48
[ 2438-80-4 ]
[ 75096-43-4 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4373,4376

49
[ 2438-80-4 ]
[ 19342-56-4 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4373,4376

50
[ 2438-80-4 ]
[ 921-90-4 ]

Reference： [1]Journal of the Chemical Society,1958,p. 1414,1416
[2]Journal of the Chemical Society,1958,p. 1414,1416

51
[ 2438-80-4 ]
[ 115936-54-4 ]

Reference： [1]Journal of the Chemical Society,1958,p. 1414,1416

52
[ 2438-80-4 ]
O⁵-methyl-L-lyxo-6-deoxy-[2]hexosulose-bis-phenylhydrazone [ No CAS ]

Reference： [1]Journal of the Chemical Society,1958,p. 1414,1416

53
[ 2438-80-4 ]
[ 63848-11-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1944,vol. 555,p. 26,35

54
[ 2438-80-4 ]
[ 14917-71-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1944,vol. 555,p. 26,35

55
[ 2438-80-4 ]
[ 24333-02-6 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1658

56
[ 2438-80-4 ]
[ 30254-29-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1970,vol. 738,p. 68 - 78

57
[ 2438-80-4 ]
[ 58917-26-3 ]

Reference： [1]Canadian Journal of Chemistry,1977,vol. 55,p. 3280 - 3287

58
[ 2438-80-4 ]
[ 60609-59-8 ]

Reference： [1]Canadian Journal of Chemistry,1977,vol. 55,p. 3280 - 3287

59
[ 79-06-1 ]
[ 2438-80-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	In water; isopropyl alcohol;	Preparation of polymer 23 Monomer 22 (460 mg, 1.44 mmol) and acrylamide (511 mg, 7.21 mmol) were dissolved in 4 mL of pure water and the solution was purged with nitrogen. Then, 5 mg of V-50 initiator was added and the solution was heated to 60 C. The solution became viscous within 30 minutes and heating was stopped. After 24 h, the viscous solution was added to isopropanol dropwise. The polymer was precipitated as a white mass which was filtered and dried in vacuum at room temperature for 48 h. The polymer was obtained as a white solid (640 mg) in 66% yield.
		Preparation of polymer 17a Pure monomer 14a (300 mg) and acrylamide (217 mg) were polymerized by the method described for the preparation of polymer 16a in Example 4, yielding 470 mg of polymer as a white powder.

Reference： [1]Patent: US5891862,1999,A
[2]Patent: US5891862,1999,A

60
[ 112-16-3 ]
[ 2438-80-4 ]
[ 13224-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap; In pentane;	Example B Synthesis of 1,2,3,4,6-Penta-O-lauroyl-alpha/beta-L-fucopyranoside 1 To a suspension of L-fucose (11.8 g, 71.8 mmol), pyridine (28.4 g, 358 mmol), and 4-dimethylaminopyridine (cat.) in pentane (400 mL) under argon atmosphere, was added lauroyl chloride (78.5 g, 358 mmol) at -78 C. The mixture was allowed to reach ambient temperature. The resulting white slurry slowly dissolved and a fine precipitate of pyridinium hydrochloride formed. After 24 h, the pyridinium hydrochloride was filtered off and the pentane solution was concentrated. Column chromatography (SiO2, pentane/EtOAc 15:1) gave 1 (68 g, quant. yield). 1 H-NMR for the alpha-anomer: delta 6.35 (d, 1H, J 2.9 Hz, H-1), 5.34 (m, 3H, H-2, H-3, H4), 4.26 (br q, 1H, J 6.2 Hz, H-5), 2.42 (t, 3H, J 7.5 Hz, --CH2 CO--), 2.37 (t, 3H, J 7.5 Hz, --CH2 CO--), 2.21 (m, 6H, --CH2 CO--), 1.14 (d, 3H, J 6.5 Hz, H-6), 0.88 (t, 12H, J 7.0 Hz, --CH2 CH3). 1 H-NMR for the beta-anomer: delta 5.69 (d, 1H, J 8.2 Hz, H-1), 5.32 (dd, 1H, J 8.2 and 10.4 Hz, H-2), 5.28 (dd, 1H, J 1.0 and 3.2 Hz, H-4), 5.08 (dd, 1H, J 3.4 and 10.4 Hz, H-3), 3.95 (br q, 1H, J 6.6 Hz, H-5), 2.42 (br t, 3H, J 7.5 Hz, --CH2 CO--), 2.34 (dt, 3H, J 4.5 and 7.5 Hz, --CH2 CO--), 2.21 (m, 6H, --CH2 CO--), 1.21 (d, 3H, J 6.5 Hz, H-6), 0.88 (t, 12H, J 7.0 Hz, --CH2 CH3).

Reference： [1]Patent: US6087339,2000,A

61
1,6-dideoxy-1-hydrazino-L-galactitol [ No CAS ]
[ 2438-80-4 ]
[ 179821-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; acetic anhydride; sodium hydrogencarbonate; acetic acid; In methanol; water; hydrazine;	O. 1,6-dideoxy-1-hydrazino-L-galactitol heptaacetate 6-deoxy-L-galactose (0.100 mmol) was dissolved in 1.0 mL anhydrous hydrazine (Pierce or Aldrich Chemical Company) in a Pierce reacti-vial, and capped under nitrogen with a cap having a Pierce Tuf-bond teflon-silicone seal. The sample, after sitting at room temperature for 16 hours, was converted to the hydrazone derivative of 6-deoxy-L-galactose which was evaporated to a resin-like material in a Speed-Vac concentrator. The sample was quantitatively transferred in a 1.0 mL volume of water into a 20 mL test tube, and 100 mg of sodium borohydride was added, which reduced the molecule to 1,6-dideoxy-1-hydrazino-L-galactitol. After 24 hours, the sample was placed in an ice-water bath and 0.200 mL of glacial acetic was added, dropwise, over about a 30 second interval. The sample was diluted with 1.0 mL water. To it was added 200 mg of sodium bicarbonate and the bicarbonate was permitted to dissolve, with occasional mixing. Then, 0.100 mL acetic anhydride was added, followed by gentle swirling to dissolve all of it. After 10 minutes, another 0.100 mL acetic anhydride was added, the solution gently swirled to dissolve it, and, after an additional 50 minutes, the sample was diluted with 5.0 mL water and loaded on a column containing 10-12mL of well-washed Dowex AG1-XS, 100-200 mesh, H+ form, to remove sodium. The column was washed with five additional washes of 10 mL water. The total elude was rotary evaporated to near dryness, and then rotary evaporated to dryness five times with 20 mL of 1% acetic acid in methanol, and three times with 20 mL methanol alone, to remove boric acid, thereby resulting in 1-(N,N'-diacetylhydrazino)-1,6-dideoxy-L-galactitol. This sample contained some additional N,N'-diacetylhydrazine.

Reference： [1]Patent: US5585473,1996,A

62
[ 2438-80-4 ]
[ 815-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In methanol;	EXAMPLE 21 6-Deoxy-L-galactose hydrazone, compound with platinum chloride (1:1) A solution of 4.0 g of 6-deoxy-L-galactose in 10 ml of methanol and 10 ml of hydrazine hydrate was stirred overnight, then evaporated to dryness, giving 4.4 g of 6-deoxy-L-galactose hydrazone.

Reference： [1]Patent: US4587331,1986,A

63
[ 2438-80-4 ]
[ 124-30-1 ]
[ 89681-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 22 N-Octadecyl-L-fucopyranosylamine 3.26 g of L-fucose and 5.38 g of stearylamine in 20 ml of ethanol are heated at 70 C., with stirring, until a clear solution has resulted. This is allowed to cool and, when crystallization is complete, the solid is filtered off with suction and washed with ethanol and ether. Yield after drying in vacuo: 4.4 g.
	In ethanol;	EXAMPLE 22 N-Octadecyl-L-fucopyranosylamine 3.26 g of L-fucose and 5.38 g of stearylamine in 20 ml of ethanol were heated to 70 C. with stirring until a clear solution had resulted. It was allowed to cool down and, after completion of crystallisation, the solid material was filtered off with suction and washed with ethanol and ether. Yield after drying in vacuo: 4.4 g.
	In ethanol;	EXAMPLE 23 N-Octadecyl-L-fucopyranosylamine 3.26 g of L-fucose and 5.38 g of stearylamine were heated at 70 C. in 20 ml of ethanol, with stirring, until a clear solution had formed. The solution was allowed to cool and, when crystallization had ended, the solid was filtered off with suction and washed with ethanol and ether. Yield after drying in vacuo: 4.4 g.

Reference： [1]Patent: US4680287,1987,A
[2]Patent: US4683222,1987,A
[3]Patent: US4710491,1987,A

64
[ 2438-80-4 ]
[ 80787-43-5 ]
benzyl m-aminobenzoate-N-L-fucoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With ammonium chloride; In methanol; water; butan-1-ol; benzene;	EXAMPLE 11 Synthesis of benzyl m-aminobenzoate-N-L-fucoside: In 20 ml of an aqueous 94% ethanolic solution, 2.1 g of benzyl m-aminobenzoate, 1.5 g of L-fucose and 0.2 g of ammonium chloride were heated under a reflux condenser to bring the raw materials into condensation, and the reaction mixture was condensed. The condensate was poured into an excess acetone, and the insoluble matter was removed by filtration. The filtrate was evaporated to dryness, and after dissolving the dried solid into an aqueous 50% ethanolic solution, the solution was subjected to thin layer chromatography using a silicagel plate. The adsorbed substance was eluted by a solvent mixture of methanol, benzene, butanol and water of a volume ratio of 5:5:10:2 and the elude was again subjected to the same chromatography to obtain the object product as a pale yellow powdery material in a yield of 19%.

Reference： [1]Patent: US4372948,1983,A

65
hexahydrobenzyl m-aminobenzoate [ No CAS ]
[ 2438-80-4 ]
hexahydrobenzyl m-aminobenzoate-N-L-fucoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.5%	With ammonium chloride;	EXAMPLE 22 Synthesis of hexahydrobenzyl m-aminobenzoate-N-L-fucoside: In 20 ml of an aqueous 94% ethanolic solution, 2.1 g of hexahydrobenzyl m-aminobenzoate, 1.5 g of L-fucose and 0.2 g of ammonium chloride were heated under a reflux condenser to bring the raw materials into condensation. The reaction mixture was then condensed to dryness. The dried matter was subjected to the same procedures including the thin layer chromatography as in Example 10 to obtain a pale yellow powdery substance in a yield of 24.5%.

Reference： [1]Patent: US4372948,1983,A

66
[ 2438-80-4 ]
[ 77-76-9 ]
[ 24577-96-6 ]

Yield	Reaction Conditions	Operation in experiment
2.28 g (59%)	With hydrogenchloride; toluene-4-sulfonic acid; In N-methyl-acetamide; methanol; hexane; chloroform; acetone;	(l) Methyl 6-deoxy-3,4-O-isopropylidene-alpha-L-galactopyranoside A suspension of L-fucose (2.90 g) in methanol (40 ml) containing l% hydrogen chloride was heated for 8 hours under reflux. The resulting homogeneous solution was cooled to room temperature, neutralized with the addition of basic lead carbonate and then filtered. The filtrate was concentrated to give a colorless solid (3.04 g) comprising mixture of methyl fucosides. The solid was dissolved in dry dimethylformamide (40 ml), to which were added 2,2-dimethoxypropane (7.8l g) and anhydrous p-toluenesulfonic acid (870 mg) and the reaction was conducted at room temperature for 2 hours. The reaction solution was neutralized with sodium hydrogen carbonate and then filtered to remove the insoluble matters. The filtrate was concentrated in vacuo and the residue obtained was dissolved in chloroform (l00 ml). The resulting solution was washed with a saturated aqueous sodium hydrogen carbonate solution and then with an aqueous l0% sodium chloride solution and then concentrated. The residue was treated by silica gel column chromatography on a column of silica gel (400 ml) using a mixture of hexane and acetone (2:l by volume) as eluent (750-l200 ml), to isolate and purify the titled compound as a syrup. Yield: 2.28 g (59%). [alpha] 1H-NMR spectrum (deuterochloroform): delta 4.72 (lH, d, H-l) J1.23.5 Hz
	With sodium chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In N-methyl-acetamide; chloroform; methanol hydrochloride;	(1) Preparation of methyl 6-deoxy-3,4-0-isopropylidene-alpha-L-galactopyranoside 2.90 Grams of L-fucose was suspended in 40 ml of 1% hydrogen chloride-methanol, and the suspension was heated under reflux for 8 hours. The resulting homogeneous solution was cooled to room temperature, and then neutralized with the addition of basic lead carbonate. The mixture was filtered, and the filtrate was concentrated to obtain 3.04 g of a colorless solid composed of a methylfucoside mixture. This solid was dissolved in 40 ml of anhydrous dimethylformamide, and 7.81 g of 2,2-dimethoxypropane and 870 mg of anhydrous p-toluenesulfonic acid were added, followed by reacting the mixture for 2 hours at room temperature. The reaction mixture was neutralized with the addition of sodium hydrogencarbonate, and the insolubles were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was dissolved in 100 ml of chloroform. The resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and a 10% aqueous solution of sodium chloride, and then concentrated. The residue was subjected to 400 ml silica gel column chromatography (developer system: hexane-acetone = 3:1) for separation and purification, thereby obtaining 2.28 g (59%) of the captioned compound as a syrup. [alpha]

Reference： [1]Patent: EP230013,1987,A1
[2]Patent: EP275431,1988,A1

67
[ 67-56-1 ]
[ 2438-80-4 ]
[ 14687-15-1 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2009,vol. 73,p. 562 - 569
[2]Physical Chemistry Chemical Physics,2007,vol. 9,p. 4444 - 4451

68
[ 2438-80-4 ]
[ 771-97-1 ]
[ 1027103-28-1 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 3848 - 3853

69
[ 2438-80-4 ]
[ 1101863-07-3 ]
(3S)-O-(N-methoxy-N-α-L-fucosylglycyl)betulinic acid [ No CAS ]
(3S)-O-(N-methoxy-N-β-L-fucosylglycyl)betulinic acid [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 461 - 464

70
fucoidan [ No CAS ]
[ 58-86-6 ]
[ 3458-28-4 ]
[ 2438-80-4 ]
[ 50-99-7 ]
[ 59-23-4 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2009,vol. 73,p. 961 - 964

71
[ 2438-80-4 ]
[ 77-76-9 ]
5-deoxy-2,3-O-isopropylidene-L-lyxofuranose [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 1192 - 1202

72
[ 1202249-78-2 ]
[ 66347-26-0 ]
[ 2438-80-4 ]
[ 1202249-91-9 ]