allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside

Base Information

• Chemical Name: allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside
• CAS No.: 150799-03-4
• Molecular Formula: C₅₅H₈₇NO₉
• Molecular Weight: 906.297

Synonyms:

Chemical Property of allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside

There total 6 articles about allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside 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:

(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one (114827-87-1) → allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside (150799-03-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 70.8 percent / Ag₂O / dimethylformamide / Ambient temperature

2: LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) RT, 30 min

3: 79.8 percent / dicyclohexylcarbodiimide (DCC), DMAP / CH₂Cl₂ / 10 h / Ambient temperature

4: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 2 h / Ambient temperature

5: Girard-T / ethanol / 3 h / Ambient temperature

6: DMAP, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; Trimethylammoniumessigsaeurebetain-methylester-chlorid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.66.1709

Reference yield:

(1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one (151557-90-3) → allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside (150799-03-4)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) RT, 30 min

2: 79.8 percent / dicyclohexylcarbodiimide (DCC), DMAP / CH₂Cl₂ / 10 h / Ambient temperature

3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 2 h / Ambient temperature

4: Girard-T / ethanol / 3 h / Ambient temperature

5: DMAP, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; Trimethylammoniumessigsaeurebetain-methylester-chlorid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1246/bcsj.66.1709

Reference yield:

(R)-3-Benzyloxy-tetradecanoic acid (2S,3S,4S,5S)-5-allyloxy-4-amino-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-ylmethyl ester (150799-01-2) → allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside (150799-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Girard-T / ethanol / 3 h / Ambient temperature

2: DMAP, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

With dmap; Trimethylammoniumessigsaeurebetain-methylester-chlorid; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1246/bcsj.66.1709

upstream raw materials:

(R)-3-benzyloxytetradecanoic acid

allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-2,3-dideoxy-3-C-hydroxymethyl-5,6-O-isopropylidene-α-D-mannofuranoside

(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-<(1R)-1,2-isopropyridenedioxyethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

(1R,2S,4S,5S)-4-allyloxy-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-O-isopropylideneethyl>-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

Downstream raw materials:

2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-5,6-O-isopropylidene-α-D-mannofuranoside

allyl 2-<(3R)-3-(benzyloxy)tetradecanoylamino>-3-C-<<(3R)-3-(benzyloxy)tetradecanoyloxy>methyl>-2,3-dideoxy-4,6-O-isopropylidene-D-mannopyranoside

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