Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 455333-62-7
• Molecular Formula: C₄₅H₅₉N₃O₁₂S
• Molecular Weight: 866.042

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 19 articles about Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-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: 74.0%

ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (156626-44-7) + Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester → Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester (455333-62-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 ℃;

DOI:10.1016/S0040-4039(02)00491-4

Reference yield:

allyl α-D-isopropylidene-α-D-fucopyranoside (201858-29-9) → Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester (455333-62-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: PhC(OEt)3; CSA / acetonitrile

1.2: pyridine

1.3: 72 percent / AcOH / H₂O

2.1: 84 percent / BF₃*Et₂O

3.1: 87 percent / NaOMe / methanol

4.1: DABCO / (Ph₃P)3RhCl / ethanol; H₂O; toluene

5.1: CSA / CH₂Cl₂

6.1: 100 percent / NaOMe / methanol

7.1: pyridine

8.1: LiN₃ / dimethylformamide

9.1: TFA / CH₂Cl₂; H₂O

10.1: pyridine

11.1: hydrazine acetate / dimethylformamide

11.2: 91 percent / K₂CO₃ / CH₂Cl₂

12.1: 63 percent / TMSOTf / CH₂Cl₂ / -40 °C

13.1: 83 percent / NBS / H₂O; acetone

14.1: 100 percent / K₂CO₃ / CH₂Cl₂

15.1: 74 percent / TMSOTf / CH₂Cl₂ / -60 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; N-Bromosuccinimide; lithium azide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; hydrazinium monoacetate; potassium carbonate; triethoxymethylbenzene; trifluoroacetic acid; Wilkinson's catalyst; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(02)00491-4

Reference yield:

Benzoic acid (2R,3S,4R,5R,6S)-6-allyloxy-5-hydroxy-4-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (455333-52-5) → Acetic acid (2S,3R,4S,5R,6R)-5-azido-2-[(2S,3R,4R,5S,6S)-3-benzyloxy-2-((2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-4-yloxy)-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy]-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester (455333-62-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: DABCO / (Ph₃P)3RhCl / ethanol; H₂O; toluene

2.1: CSA / CH₂Cl₂

3.1: 100 percent / NaOMe / methanol

4.1: pyridine

5.1: LiN₃ / dimethylformamide

6.1: TFA / CH₂Cl₂; H₂O

7.1: pyridine

8.1: hydrazine acetate / dimethylformamide

8.2: 91 percent / K₂CO₃ / CH₂Cl₂

9.1: 63 percent / TMSOTf / CH₂Cl₂ / -40 °C

10.1: 83 percent / NBS / H₂O; acetone

11.1: 100 percent / K₂CO₃ / CH₂Cl₂

12.1: 74 percent / TMSOTf / CH₂Cl₂ / -60 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; N-Bromosuccinimide; lithium azide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; hydrazinium monoacetate; potassium carbonate; trifluoroacetic acid; Wilkinson's catalyst; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(02)00491-4

upstream raw materials:

ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

allyl α-D-isopropylidene-α-D-fucopyranoside

phenyl 4-O-methyl-1-thio-α-L-rhamnopyranoside

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