(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

Base Information

Chemical Name:(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol
CAS No.:181960-87-2
Molecular Formula:C₄₁H₄₆N₂O₁₀
Molecular Weight:726.824
Hs Code.:

(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

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Chemical Property of (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

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Technology Process of (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

There total 7 articles about (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol 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:

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 181960-87-2
(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / NaN₃ / acetonitrile / 12 h / Heating

2: 69 percent / hydrogen / Pd(OH)2-on-charcoal / tetrahydrofuran; ethanol; H₂O / 3 h / 24 °C

3: 217 mg / tetrahydrofuran / 48 h / 25 °C

4: 84 percent / KOH / aq. ethanol / 0.5 h / 25 °C

5: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) triethylamine / 1.) acetonitrile, 0-5 deg C, 2 h, 2.) acetonitrile, 0-5 deg C, 30 min

With potassium hydroxide; sodium azide; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; hydrogen; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; water; acetonitrile;
DOI:10.1016/0008-6215(96)00090-0

Reference yield:

: 604-69-3
β-D-glucose pentaacetate

: 181960-87-2
(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / Me₃SiN₃, SnCl₄ / CH₂Cl₂ / 0.5 h / 24 °C

2: 69 percent / hydrogen / Pd(OH)2-on-charcoal / tetrahydrofuran; ethanol; H₂O / 3 h / 24 °C

3: 217 mg / tetrahydrofuran / 48 h / 25 °C

4: 84 percent / KOH / aq. ethanol / 0.5 h / 25 °C

5: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) triethylamine / 1.) acetonitrile, 0-5 deg C, 2 h, 2.) acetonitrile, 0-5 deg C, 30 min

With potassium hydroxide; trimethylsilylazide; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; hydrogen; tin(IV) chloride; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1016/0008-6215(96)00090-0

Reference yield:

: 20379-61-7
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide

: 181960-87-2
(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) hydrogen, 2.) silica gel / 1.) Pd(OH)2-on-charcoal / 1.) THF, water, 24 deg C, 2 h

2: 217 mg / tetrahydrofuran / 48 h / 25 °C

3: 84 percent / KOH / aq. ethanol / 0.5 h / 25 °C

4: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) triethylamine / 1.) acetonitrile, 0-5 deg C, 2 h, 2.) acetonitrile, 0-5 deg C, 30 min

With potassium hydroxide; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; hydrogen; silica gel; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; ethanol;
DOI:10.1016/0008-6215(96)00090-0