(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol
CAS No.:147158-33-6
Molecular Formula:C₃₅H₅₂N₄O₉SeSi
Molecular Weight:779.865
Hs Code.:

(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

Synonyms:(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

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Technology Process of (2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

There total 11 articles about (2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol 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: 87.0%

: 147158-39-2
C₅₀H₅₈N₄O₁₂SeSi

: 147158-33-6
(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

Guidance literature:: With hydrazine hydrate; In ethanol; at 100 ℃; for 12h;
DOI:10.1021/ja00058a060 DOI:10.1021/ja00090a018

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 147158-33-6
(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 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

With 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:

: 147254-13-5
(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 147158-33-6
(2S,3R,4R,5R,6S)-5-Amino-6-[(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-2-phenylselanylmethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 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

With 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