{(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester
• CAS No.: 158421-36-4
• Molecular Formula: C₄₃H₆₀N₂O₁₁SeSi
• Molecular Weight: 888.002

Synonyms:{(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester

Chemical Property of {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester

There total 15 articles about {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-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: 91.0%

{(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Azido-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester (147158-40-5) → {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester (158421-36-4)

Guidance literature:

With Benzeneselenol; triethylamine; at 55 ℃; for 12h;

DOI:10.1021/ja00058a060 DOI:10.1021/ja00090a018

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester (158421-36-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 15 h / Heating

2: 98 percent / triethylamine, benzeneselenol / 2.5 h / 60 °C

3: 1.) triethylamine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) dichloromethane, 0 deg C, 10 min, 2.) toluene, 100 deg C, 1.5 h

4: 95 percent / triethylamine / 1,2-dimethoxy-ethane / 10 h / 90 °C

5: triethylamine trihydrofluoride / acetonitrile / 6 h / 23 °C

6: 1.) 4-A molecular sieves, 2.) trifluoromethanesulfonic acid / 1.) toluene, 23 deg C, 2 h, 2.) toluene, -20 deg C

7: 87 percent / hydrazine hydrate / ethanol / 12 h / 100 °C

8: 91 percent / pyridine / 0.5 h / 0 °C

9: 91 percent / benzeneselenol, triethylamine / 12 h / 55 °C

With pyridine; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine trihydrofluoride; Benzeneselenol; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/ja00090a018

Reference yield:

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside (147254-13-5) → {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester (158421-36-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / bromotrichloromethane / 2.5 h / 0 °C / Irradiation

2: 89 percent / diisopropylethylamine / CH₂Cl₂ / 15 h / Heating

3: 98 percent / triethylamine, benzeneselenol / 2.5 h / 60 °C

4: 1.) triethylamine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) dichloromethane, 0 deg C, 10 min, 2.) toluene, 100 deg C, 1.5 h

5: 95 percent / triethylamine / 1,2-dimethoxy-ethane / 10 h / 90 °C

6: triethylamine trihydrofluoride / acetonitrile / 6 h / 23 °C

7: 1.) 4-A molecular sieves, 2.) trifluoromethanesulfonic acid / 1.) toluene, 23 deg C, 2 h, 2.) toluene, -20 deg C

8: 87 percent / hydrazine hydrate / ethanol / 12 h / 100 °C

9: 91 percent / pyridine / 0.5 h / 0 °C

10: 91 percent / benzeneselenol, triethylamine / 12 h / 55 °C

With pyridine; Bromotrichloromethane; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine trihydrofluoride; Benzeneselenol; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/ja00090a018

upstream raw materials:

{(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Azido-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester

Benzyloxymethyl chloride

benzyl chloroformate

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Downstream raw materials:

C₄₇H₆₄N₂O₁₃SeSi

tunicamycin V

{(2S,3R,4R,5R)-2-[(4aR,6R,7R,8R,8aR)-7-Acetylamino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-methylene-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester

Acetic acid (3R,4R,5R,6S)-6-[(4aR,6R,7R,8R,8aR)-7-acetylamino-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-5-benzyloxycarbonylamino-4-benzyloxymethoxy-2-methylene-tetrahydro-pyran-3-yl ester

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