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

Base Information

• Chemical Name: methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate
• CAS No.: 246864-34-6
• Molecular Formula: C₄₄H₅₃NO₉
• Molecular Weight: 739.906
• Mol file: 246864-34-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R)-2-tert-Butoxycarbonylamino-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid → methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate (246864-34-6)

Guidance literature:

DOI:10.1039/a905014k

Reference yield:

(S)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine (246864-27-7) → methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate (246864-34-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / K₂CO₃ / acetone / 4.4 h / Heating

2: mCPBA; Na₂HPO₄ / CH₂Cl₂ / 3 h

3: 37 percent / KOH; Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 60 °C

4: 82 percent / tosylhydrazine; NaOAc / CH₂Cl₂ / 16 h / 85 °C

5: 0.05 g / Jones reagent / acetone / 6.25 h / 5 - 20 °C

6: 0.031 g / diethyl ether / 20 °C

With aluminum oxide; potassium hydroxide; disodium hydrogenphosphate; jones reagent; dibromodifluoromethane; sodium acetate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; In diethyl ether; dichloromethane; acetone; tert-butyl alcohol; 3: Ramberg-Baecklund rearrangement;

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

Reference yield:

(4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine (441044-67-3) → methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate (246864-34-6)

Guidance literature:

Multi-step reaction with 5 steps

1: mCPBA; Na₂HPO₄ / CH₂Cl₂ / 3 h

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

3: 82 percent / tosylhydrazine; NaOAc / CH₂Cl₂ / 16 h / 85 °C

4: 0.05 g / Jones reagent / acetone / 6.25 h / 5 - 20 °C

5: 0.031 g / diethyl ether / 20 °C

With aluminum oxide; potassium hydroxide; disodium hydrogenphosphate; jones reagent; dibromodifluoromethane; sodium acetate; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; In diethyl ether; dichloromethane; acetone; tert-butyl alcohol; 2: Ramberg-Baecklund rearrangement;

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

upstream raw materials:

diazomethane

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

(S)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

(S)-S-acetyl-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine