[5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester
• CAS No.: 83663-08-5
• Molecular Formula: C₄₆H₅₄N₄O₁₁
• Molecular Weight: 838.955

Synonyms:

Chemical Property of [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester

There total 7 articles about [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester 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:

(3R,4S,5R,6R)-2-Allyloxy-3-amino-6-hydroxymethyl-5-(2-methoxy-ethoxymethoxy)-tetrahydro-pyran-4-ol (83663-05-2) → [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester (83663-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / EtOCOCl, triethylamine / tetrahydrofuran

2: 66 percent / BaO-Ba(OH)2 / dimethylformamide / 15 h / Ambient temperature

3: ZnBr₂ / CH₂Cl₂

4: Zn(powder) / methanol / 3 h / Ambient temperature

With barium dihydroxide; chloroformic acid ethyl ester; triethylamine; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87506-1

Reference yield:

allyl 6-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-D-gulopyranoside (83663-04-1) → [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester (83663-08-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / ethyldiisopropylamine / dioxane / 4 h / 70 °C

2: Ba(OH)2 / ethanol; H₂O / 1 h / Heating

3: 91 percent / EtOCOCl, triethylamine / tetrahydrofuran

4: 66 percent / BaO-Ba(OH)2 / dimethylformamide / 15 h / Ambient temperature

5: ZnBr₂ / CH₂Cl₂

6: Zn(powder) / methanol / 3 h / Ambient temperature

With barium dihydroxide; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87506-1

Reference yield:

Acetic acid (1R,2R,4S,5R,6R)-4-allyloxy-5-benzyloxycarbonylamino-3,7-dioxa-bicyclo[4.1.0]hept-2-ylmethyl ester → [5-((2S,3R,4S,5R,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester (83663-08-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / 2.) H₂O / acetic acid

2: 73 percent / ethyldiisopropylamine / dioxane / 4 h / 70 °C

3: Ba(OH)2 / ethanol; H₂O / 1 h / Heating

4: 91 percent / EtOCOCl, triethylamine / tetrahydrofuran

5: 66 percent / BaO-Ba(OH)2 / dimethylformamide / 15 h / Ambient temperature

6: ZnBr₂ / CH₂Cl₂

7: Zn(powder) / methanol / 3 h / Ambient temperature

With barium dihydroxide; water; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87506-1

upstream raw materials:

2-chloroacetylisocyanate

(3R,4S,5R,6R)-2-Allyloxy-3-amino-6-hydroxymethyl-5-(2-methoxy-ethoxymethoxy)-tetrahydro-pyran-4-ol

allyl 6-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-D-gulopyranoside

Acetic acid (3aR,4S,6R,7R,7aS)-4-allyloxy-7-(2-methoxy-ethoxymethoxy)-2-oxo-hexahydro-pyrano[3,4-d]oxazol-6-ylmethyl ester

Downstream raw materials:

[5-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-benzyloxymethyl-5-carbamoyloxy-2-isothiocyanato-tetrahydro-pyran-3-ylcarbamoyl)-4-benzyloxycarbonylamino-pentyl]-carbamic acid benzyl ester

4-Nitro-benzoic acid (2S,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-3-(3,6-bis-benzyloxycarbonylamino-hexanoylamino)-5-carbamoyloxy-tetrahydro-pyran-2-yl ester

C₆₂H₇₆N₈O₁₅S

streptothricin F

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