Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
CAS No.:647021-32-7
Molecular Formula:C₄₄H₅₀Cl₃NO₁₄
Molecular Weight:923.238
Hs Code.:

Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

There total 11 articles about Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl 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: 85.0%

: 83921-79-3
allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

: 647021-29-2
Acetic acid (3aR,5R,6S,7S,7aR)-6-acetoxy-5-acetoxymethyl-2-trichloromethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester

: 647021-32-7
Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -30 - -10 ℃;
DOI:10.1021/ol0359620

Reference yield:

: 2873-29-2
D-glucal triacetate

: 647021-32-7
Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 81 percent / BF₃*Et₂O / CH₂Cl₂ / -30 - 20 °C

2.1: 90 percent / potassium carbonate / methanol; H₂O / 16 h / 20 °C

3.1: 95 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

4.1: 90 percent / DBU / CH₂Cl₂ / -78 - 20 °C

5.1: 72 percent / potassium carbonate / diphenyl ether / 170 - 197 °C

6.1: quinuclidine-N-oxide monohydrate; OsO₄ / CH₂Cl₂ / 48 h / 20 °C

6.2: 85 percent / sodium sulfite / CH₂Cl₂ / 4 h / 50 °C

7.1: 91 percent / HCl / methanol / 5 h / 20 °C

8.1: 99 percent / pyridine; 4-(dimethylamino)pyridine / 48 h / 20 °C

9.1: DDQ / CH₂Cl₂; H₂O / 20 °C

10.1: methanesulfonic anhydride; triethylamine / acetonitrile / 1.33 h / 20 °C

11.1: 85 percent / molecular sieves 4 Angstroem; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -30 - -10 °C

With pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; quinuclidine-N-oxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Methanesulfonic anhydride; In methanol; diphenylether; dichloromethane; water; acetonitrile; 5.1: Overman rearrangement;
DOI:10.1021/ol0359620

Reference yield:

: 647021-59-8
(2R,3S,6S)-2-Hydroxymethyl-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-ol

: 647021-32-7
Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: 90 percent / DBU / CH₂Cl₂ / -78 - 20 °C

3.1: 72 percent / potassium carbonate / diphenyl ether / 170 - 197 °C

4.1: quinuclidine-N-oxide monohydrate; OsO₄ / CH₂Cl₂ / 48 h / 20 °C

4.2: 85 percent / sodium sulfite / CH₂Cl₂ / 4 h / 50 °C

5.1: 91 percent / HCl / methanol / 5 h / 20 °C

6.1: 99 percent / pyridine; 4-(dimethylamino)pyridine / 48 h / 20 °C

7.1: DDQ / CH₂Cl₂; H₂O / 20 °C

8.1: methanesulfonic anhydride; triethylamine / acetonitrile / 1.33 h / 20 °C

9.1: 85 percent / molecular sieves 4 Angstroem; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -30 - -10 °C

With pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; quinuclidine-N-oxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Methanesulfonic anhydride; In methanol; diphenylether; dichloromethane; water; acetonitrile; 3.1: Overman rearrangement;
DOI:10.1021/ol0359620