2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

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Chemical Name:2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose
CAS No.:171815-18-2
Molecular Formula:C₄₁H₄₆N₂O₁₀
Molecular Weight:726.824
Hs Code.:

Synonyms:2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

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Chemical Property of 2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

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Technology Process of 2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

There total 15 articles about 2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose 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

: 171815-18-2
2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 14 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

14: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 1 h

With hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; 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

: 171815-18-2
2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 10 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

10: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 1 h

With hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; 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

: 171815-18-2
2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 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

7: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 1 h

With hydrogenchloride; sodium azide; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; hydrogen; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00124a023