{(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

Base Information

Chemical Name:{(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
CAS No.:147158-34-7
Molecular Formula:C₃₉H₅₆N₂O₁₂Si
Molecular Weight:772.965
Hs Code.:

{(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

Synonyms:{(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

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Chemical Property of {(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

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Technology Process of {(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

There total 18 articles about {(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 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: 92.0%

: 158421-38-6
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

: 147158-34-7
{(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

Guidance literature:: With potassium carbonate; In methanol; at 23 ℃; for 2h;
DOI:10.1021/ja00090a018

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 147158-34-7
{(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

Guidance literature:: Multi-step reaction with 12 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

10: 91 percent / pyridine / 2.5 h / 60 °C

11: 1.) m-chloroperoxybenzoic acid, 2.) Me₂S, triethylamine / 1.) CCl₄, from -15 deg C to 0 deg C, 50 min, 2.) CCl₄, 65 deg C, 10 h

12: 92 percent / K₂CO₃ / methanol / 2 h / 23 °C

With pyridine; dimethylsulfide; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine trihydrofluoride; Benzeneselenol; potassium carbonate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; 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

: 147158-34-7
{(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

Guidance literature:: Multi-step reaction with 13 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

11: 91 percent / pyridine / 2.5 h / 60 °C

12: 1.) m-chloroperoxybenzoic acid, 2.) Me₂S, triethylamine / 1.) CCl₄, from -15 deg C to 0 deg C, 50 min, 2.) CCl₄, 65 deg C, 10 h

13: 92 percent / K₂CO₃ / methanol / 2 h / 23 °C

With pyridine; dimethylsulfide; Bromotrichloromethane; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine trihydrofluoride; Benzeneselenol; potassium carbonate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ja00090a018