N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea

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Chemical Name:N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea
CAS No.:171815-17-1
Molecular Formula:C₄₁H₄₈N₂O₁₀S
Molecular Weight:760.906
Hs Code.:

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Chemical Property of N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea

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Technology Process of N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea

There total 14 articles about N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea 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:

: 54497-89-1
methyl 2,6-bis-α-D-glucopyranoside

: 171815-17-1
N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea

Guidance literature:: Multi-step reaction with 13 steps

1: P₂O₅ / CHCl₃ / 1 h / 0 °C

2: NaI, n-Bu₄NI, 4 Angstroem molecular sieves / dimethylsulfoxide / 2 h / 90 °C

3: DBU / dimethylsulfoxide / 20 h / 90 °C

4: 90 percent / NaOMe / methanol / 60 h / Heating

5: 86 percent / NaH / dimethylformamide / 1.) room temp., 30 min, 2.) room temp., 1 h

6: 2.) Ac₂O / 1.) Hg(OCOCF₃)2 / 1.) aq. acetone, room temp., 15 h, 2.) pyridine, room temp., 21 h

7: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / 0 °C

8: 91 percent / m-CPBA / CH₂Cl₂ / 88 h / Ambient temperature

9: 86 percent / H₂ / 20percent Pd(OH)2/C / methanol / 1 h / Ambient temperature

10: 86 percent / NaN₃, NH₄Cl / dimethylformamide / 13 h / 100 °C

11: H₂ / 20percent Pd(OH)2/C / methanol / 1 h / Ambient temperature

12: HCl / methanol / 0.5 h / 50 °C

13: Et₃N / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 4 A molecular sieve; hydrogen; sodium methylate; phosphorus pentoxide; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; palladium dihydroxide; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00124a023

Reference yield:

: 160835-77-8
methyl 6-deoxy-3,4-bis(O-methoxymethyl)-α-D-xylo-hex-5-enopyranoside

: 171815-17-1
N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / NaH / dimethylformamide / 1.) room temp., 30 min, 2.) room temp., 1 h

2: 2.) Ac₂O / 1.) Hg(OCOCF₃)2 / 1.) aq. acetone, room temp., 15 h, 2.) pyridine, room temp., 21 h

3: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / 0 °C

4: 91 percent / m-CPBA / CH₂Cl₂ / 88 h / Ambient temperature

5: 86 percent / H₂ / 20percent Pd(OH)2/C / methanol / 1 h / Ambient temperature

6: 86 percent / NaN₃, NH₄Cl / dimethylformamide / 13 h / 100 °C

7: H₂ / 20percent Pd(OH)2/C / methanol / 1 h / Ambient temperature

8: HCl / methanol / 0.5 h / 50 °C

9: Et₃N / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; acetic anhydride; sodium hydride; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00124a023

Reference yield:

: 171815-12-6
<1S-(1α,2β,3α,4β)>-4-(Benzyloxy)-2,3-bis(methoxymethoxy)-5-cyclohexen-1-ol

: 171815-17-1
N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / m-CPBA / CH₂Cl₂ / 88 h / Ambient temperature

2: 86 percent / H₂ / 20percent Pd(OH)2/C / methanol / 1 h / Ambient temperature

3: 86 percent / NaN₃, NH₄Cl / dimethylformamide / 13 h / 100 °C

4: H₂ / 20percent Pd(OH)2/C / methanol / 1 h / Ambient temperature

5: HCl / methanol / 0.5 h / 50 °C

6: Et₃N / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With hydrogenchloride; sodium azide; hydrogen; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00124a023