[(3S,4S,5S,6R)-4,5,6-triacetyloxy-3-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl]amino]cyclohexen-1-yl]methyl acetate

Base Information

Chemical Name:[(3S,4S,5S,6R)-4,5,6-triacetyloxy-3-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl]amino]cyclohexen-1-yl]methyl acetate
CAS No.:80943-42-6
Molecular Formula:C₂₆H₃₇NO₁₄
Molecular Weight:587.578
Hs Code.:
DSSTox Substance ID:DTXSID601100354

Synonyms:80943-42-6;DTXSID601100354;(1S,2S,3R,6S)-4-(Acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl)amino)cyclohex-4-ene-1,2,3-triyl triacetate;alpha-D-Glucopyranoside, methyl 4,6-dideoxy-4-[[4,5,6-tris(acetyloxy)-3-[(acetyloxy)methyl]-2-cyclohexen-1-yl]amino]-, 2,3-diacetate, [1S-(1alpha,4alpha,5beta,6alpha)]-

Suppliers and Price of [(3S,4S,5S,6R)-4,5,6-triacetyloxy-3-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl]amino]cyclohexen-1-yl]methyl acetate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of [(3S,4S,5S,6R)-4,5,6-triacetyloxy-3-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl]amino]cyclohexen-1-yl]methyl acetate

Chemical Property:

XLogP3:-0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:16
Exact Mass:587.22140485
Heavy Atom Count:41
Complexity:1040

Purity/Quality:: 95% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1C(C(C(C(O1)OC)OC(=O)C)OC(=O)C)NC2C=C(C(C(C2OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C
Isomeric SMILES:C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC)OC(=O)C)OC(=O)C)N[C@H]2C=C([C@H]([C@@H]([C@H]2OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C

Technology Process of [(3S,4S,5S,6R)-4,5,6-triacetyloxy-3-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl]amino]cyclohexen-1-yl]methyl acetate

There total 5 articles about [(3S,4S,5S,6R)-4,5,6-triacetyloxy-3-[[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl]amino]cyclohexen-1-yl]methyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 23.6%

: 129371-85-3
methyl 2,3,2',3',4',7'-hexa-O-acetyl-4-<(1S)-(1,2,4/3,5,6)-6-dideoxy-chloro-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexylamino>-4,6-dideoxy-α-D-glucopyranoside

: 80943-42-6
methyl 2,3,4',5',6',7'-hexa-O-acetyl-4,6-dideoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino>-α-D-glucopyranoside

: 129371-84-2
methyl 2,3,6,2',3',4',7'-hepta-O-acetyl-4-deoxy-4-<(1S)-(1,2,4,6/3,5)-2,3,4-trihydroxy-5-hydroxymethyl-1,6-cyclohexylenamino>-α-D-glucopyranoside

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 120 ℃; for 6h;
DOI:10.1016/0008-6215(90)84215-G

Reference yield:

: 129371-80-8
methyl 2,3,2',3',4'-penta-O-acetyl-4-<(1S)-(1,2,4/3,5,6)-6-chloro-5-chloromethyl-2,3,4-trihydroxycyclohexylamino>-4,6-dideoxy-α-D-glucopyranoside

: 80943-42-6
methyl 2,3,4',5',6',7'-hexa-O-acetyl-4,6-dideoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino>-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 99.5 percent / NaOAc / dimethylformamide / 40 h / 60 °C

2: 92.9 percent / conc. hydrochloric acid / tetrahydrofuran / 0.5 h / 0 °C

3: 55.4 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 6 h / 120 °C

With hydrogenchloride; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(90)84215-G

Reference yield:

: 129371-79-5
Acetic acid (1S,2S,3R,4S,5R,6S)-2,3-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-5-hydroxy-4-hydroxymethyl-cyclohexyl ester

: 80943-42-6
methyl 2,3,4',5',6',7'-hexa-O-acetyl-4,6-dideoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino>-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 24 mg / sulfuryl chloride, pyridine / 52 h / Ambient temperature

2: 99.5 percent / NaOAc / dimethylformamide / 40 h / 60 °C

3: 92.9 percent / conc. hydrochloric acid / tetrahydrofuran / 0.5 h / 0 °C

4: 55.4 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / toluene / 6 h / 120 °C

With pyridine; hydrogenchloride; sulfuryl dichloride; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(90)84215-G