5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal

Base Information

Chemical Name:5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal
CAS No.:98237-93-5
Molecular Formula:C₂₆H₃₁NO₅S₂
Molecular Weight:501.668
Hs Code.:

Synonyms:

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Chemical Property of 5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal

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Technology Process of 5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal

There total 10 articles about 5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal 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:

: 91897-27-7
methyl 3-benzyloxycarbonylamino-3-deoxy-6-O-tosyl-α-D-mannopyranoside

: 98237-93-5
5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / 10percent Pd/C / ethanol / 18 h / 3192 Torr

2: CH₃COONa / ethanol / 8 h / Heating

3: NaHCO₃ / ethanol; H₂O / 2 h / ice-cooling

4: 52 percent / aq. 0.4 M HCl / 16 h / 95 - 100 °C

5: 80 percent / BF₃*Et₂O / CHCl₃ / 0.03 h / Ambient temperature; conc. HCl, 15 min

6: 1.) p-TsOH; 2.) NaH / 1.) reflux, 20 min; 2.) DMF, 0 deg C, 20 min

With hydrogenchloride; boron trifluoride diethyl etherate; hydrogen; sodium acetate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; chloroform; water;

Reference yield:

: 98237-78-6
((2R,3S,4S,5S,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-carbamic acid benzyl ester

: 98237-93-5
5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 36 h / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol / 18 h / 3192 Torr

3: CH₃COONa / ethanol / 8 h / Heating

4: NaHCO₃ / ethanol; H₂O / 2 h / ice-cooling

5: 52 percent / aq. 0.4 M HCl / 16 h / 95 - 100 °C

6: 80 percent / BF₃*Et₂O / CHCl₃ / 0.03 h / Ambient temperature; conc. HCl, 15 min

7: 1.) p-TsOH; 2.) NaH / 1.) reflux, 20 min; 2.) DMF, 0 deg C, 20 min

With hydrogenchloride; boron trifluoride diethyl etherate; hydrogen; sodium acetate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In pyridine; ethanol; chloroform; water;

Reference yield:

: 14133-35-8
methyl 3-amino-3-deoxy-α-D-mannopyranoside hydrochloride

: 98237-93-5
5-O-benzyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-2,4-O-isopropylidene-D-mannose ethylene dithioacetal

Guidance literature:: Multi-step reaction with 8 steps

1: NaHCO₃ / ethanol; H₂O / 2 h / Ambient temperature

2: pyridine / 36 h / Ambient temperature

3: H₂ / 10percent Pd/C / ethanol / 18 h / 3192 Torr

4: CH₃COONa / ethanol / 8 h / Heating

5: NaHCO₃ / ethanol; H₂O / 2 h / ice-cooling

6: 52 percent / aq. 0.4 M HCl / 16 h / 95 - 100 °C

7: 80 percent / BF₃*Et₂O / CHCl₃ / 0.03 h / Ambient temperature; conc. HCl, 15 min

8: 1.) p-TsOH; 2.) NaH / 1.) reflux, 20 min; 2.) DMF, 0 deg C, 20 min

With hydrogenchloride; boron trifluoride diethyl etherate; hydrogen; sodium acetate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In pyridine; ethanol; chloroform; water;