[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

Base Information

Chemical Name:[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
CAS No.:83670-98-8
Molecular Formula:C₄₄H₄₉N₅O₁₀S
Molecular Weight:839.967
Hs Code.:

[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

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Chemical Property of [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

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Technology Process of [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

There total 11 articles about [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 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:

: 83663-05-2
(3R,4S,5R,6R)-2-Allyloxy-3-amino-6-hydroxymethyl-5-(2-methoxy-ethoxymethoxy)-tetrahydro-pyran-4-ol

: 83670-98-8
[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

Guidance literature:: Multi-step reaction with 8 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

5: 1.) RhCl(PPh₃)3; 2.) HgCl₂-HgO

6: 95 percent / pyridine

7: HBr / CH₂Cl₂ / 0.5 h / Ambient temperature

8: CaSO₄ / 1.) CH₂Cl₂, room temp., 30 min.; 2.) acetone

With pyridine; calcium sulfate; barium dihydroxide; RhCl(PPh₃)3; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; mercury dichloride; mercury(II) oxide; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)87506-1

Reference yield:

: 83663-04-1
allyl 6-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-D-gulopyranoside

: 83670-98-8
[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

Guidance literature:: Multi-step reaction with 10 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

7: 1.) RhCl(PPh₃)3; 2.) HgCl₂-HgO

8: 95 percent / pyridine

9: HBr / CH₂Cl₂ / 0.5 h / Ambient temperature

10: CaSO₄ / 1.) CH₂Cl₂, room temp., 30 min.; 2.) acetone

With pyridine; calcium sulfate; barium dihydroxide; RhCl(PPh₃)3; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; 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

: 83670-98-8
[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

Guidance literature:: Multi-step reaction with 11 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

8: 1.) RhCl(PPh₃)3; 2.) HgCl₂-HgO

9: 95 percent / pyridine

10: HBr / CH₂Cl₂ / 0.5 h / Ambient temperature

11: CaSO₄ / 1.) CH₂Cl₂, room temp., 30 min.; 2.) acetone

With pyridine; calcium sulfate; barium dihydroxide; RhCl(PPh₃)3; water; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; 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