methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside
CAS No.:126403-28-9
Molecular Formula:C₃₁H₃₃ClO₇S
Molecular Weight:585.118
Hs Code.:

Synonyms:methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

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Technology Process of methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

There total 3 articles about methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside 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: 94.0%

: 17314-32-8
tributyl(methylthio)stannane

: 123826-51-7
3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-α-D-mannopyranosyl trichloroacetimidate

: 126403-28-9
methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

Guidance literature:: With 3 A molecular sieve; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at -20 ℃; for 3h;
DOI:10.1016/0008-6215(89)85173-0

Reference yield:

: 121238-27-5
2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

: 126403-28-9
methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / pyridine / 4 h / -20 °C

2: 81 percent / NaHCO₃ / dimethylformamide / 18 h / 20 °C

3: 75 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 3 h / 20 °C

4: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2.5 h / -20 °C

5: 94 percent / molecular sieves AW 300, BF₃*Et₂O / 1,2-dichloro-ethane / 3 h / -20 °C

With pyridine; ammonium cerium(IV) nitrate; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(89)85173-0

Reference yield:

: 874-60-2
4-methyl-benzoyl chloride

: 126403-28-9
methyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-O-p-methylbenzoyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / pyridine / 4 h / -20 °C

2: 81 percent / NaHCO₃ / dimethylformamide / 18 h / 20 °C

3: 75 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 3 h / 20 °C

4: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2.5 h / -20 °C

5: 94 percent / molecular sieves AW 300, BF₃*Et₂O / 1,2-dichloro-ethane / 3 h / -20 °C

With pyridine; ammonium cerium(IV) nitrate; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(89)85173-0