benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

Base Information

Chemical Name:benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside
CAS No.:114894-84-7
Molecular Formula:C₂₆H₂₉NO₇
Molecular Weight:467.519
Hs Code.:

Synonyms:benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

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Chemical Property of benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

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Technology Process of benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

There total 13 articles about benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside 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: 59.0%

: 114894-87-0
((3aS,4S,6S,7S,7aS)-4-Benzyloxy-6-formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-carbamic acid benzyl ester

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 114894-84-7
benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

Guidance literature:: In dichloromethane; for 16h; Ambient temperature;
DOI:10.1016/S0040-4020(01)86850-2

Reference yield:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 114894-84-7
benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

2: 97 percent / camphorsulphonic acid / acetone / 16 h / Ambient temperature

3: pyridinium chlorochromate, molecular sieve 3 A / CH₂Cl₂ / 2 h / Ambient temperature; molecular sieve 3 A

4: sodium borohydride / ethanol / 1 h / 0 °C

5: pyridine / CH₂Cl₂ / 8 h / -20 °C

6: sodium azide / dimethylformamide / 16 h / Ambient temperature

7: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

8: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature

9: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C

10: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH₂Cl₂ / 1.5 h / Ambient temperature

11: 59 percent / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; pyridinium chlorochromate; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)86850-2

Reference yield:

: 3458-28-4
D-Mannose

: 114894-84-7
benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: 83 percent / acetyl chloride / 50 deg C for 1.5 h then room temperature for 24 h

2: 89 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

3: 97 percent / camphorsulphonic acid / acetone / 16 h / Ambient temperature

4: pyridinium chlorochromate, molecular sieve 3 A / CH₂Cl₂ / 2 h / Ambient temperature; molecular sieve 3 A

5: sodium borohydride / ethanol / 1 h / 0 °C

6: pyridine / CH₂Cl₂ / 8 h / -20 °C

7: sodium azide / dimethylformamide / 16 h / Ambient temperature

8: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

9: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature

10: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C

11: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH₂Cl₂ / 1.5 h / Ambient temperature

12: 59 percent / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; acetyl chloride; pyridinium chlorochromate; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)86850-2