Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

Base Information

Chemical Name:Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester
CAS No.:868759-69-7
Molecular Formula:C₂₉H₃₁N₃O₅S
Molecular Weight:533.648
Hs Code.:

Synonyms:Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

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Chemical Property of Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

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Technology Process of Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

There total 5 articles about Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-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: 55.0%

: 868759-68-6
Thioacetic acid S-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methanesulfonyloxy-tetrahydro-pyran-2-yl) ester

: 868759-69-7
Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 25 ℃; for 1h;
DOI:10.1055/s-2005-872244

Reference yield:

: 868759-67-5
Thioacetic acid S-((2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl) ester

: 868759-69-7
Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 2 h

2: 55 percent / NaN₃ / dimethylformamide / 1 h / 25 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;
DOI:10.1055/s-2005-872244

Reference yield:

: 868759-65-3
Chloro-acetic acid (3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester

: 868759-69-7
Thioacetic acid S-((2R,3R,4S,5R,6R)-2-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

Guidance literature:: Multi-step reaction with 4 steps

1: 42 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h

2: 73 percent / thiourea / methanol / 8 h / 50 °C

3: pyridine / 2 h

4: 55 percent / NaN₃ / dimethylformamide / 1 h / 25 °C

With pyridine; sodium azide; boron trifluoride diethyl etherate; thiourea; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2005-872244