5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol

Base Information

• Chemical Name: 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol
• CAS No.: 441044-68-4
• Molecular Formula: C₄₆H₅₇NO₈
• Molecular Weight: 751.96

Synonyms:5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol

Chemical Property of 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol

There total 10 articles about 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol 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: 82.0%

(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol (246864-29-9) → 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol (441044-68-4)

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In dichloromethane; at 85 ℃; for 16h;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol (441044-68-4)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / methanol

2: 83 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 1 h / 0 °C

3: 57 percent / NaOMe / methanol / 4 h

4: 71 percent / K₂CO₃ / acetone / 4.4 h / Heating

5: mCPBA; Na₂HPO₄ / CH₂Cl₂ / 3 h

6: 37 percent / KOH; Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 60 °C

7: 82 percent / tosylhydrazine; NaOAc / CH₂Cl₂ / 16 h / 85 °C

With aluminum oxide; potassium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; dibromodifluoromethane; di-isopropyl azodicarboxylate; sodium methylate; sodium acetate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol; 6: Ramberg-Baecklund rearrangement;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5) → 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol (441044-68-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

1.2: H₂O₂; aq. KOH

2.1: 0.674 g / PPh₃; imidazole; I₂ / toluene / 0.5 h / 70 °C

3.1: 71 percent / K₂CO₃ / acetone / 4.4 h / Heating

4.1: mCPBA; Na₂HPO₄ / CH₂Cl₂ / 3 h

5.1: 37 percent / KOH; Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 60 °C

6.1: 82 percent / tosylhydrazine; NaOAc / CH₂Cl₂ / 16 h / 85 °C

With 1H-imidazole; aluminum oxide; potassium hydroxide; disodium hydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; dibromodifluoromethane; iodine; sodium acetate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetone; toluene; tert-butyl alcohol; 5.1: Ramberg-Baecklund rearrangement;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

upstream raw materials:

(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate

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